tert-butyl 2-oxo-3H-benzimidazole-1-carboxylate

Base Information

• Chemical Name: tert-butyl 2-oxo-3H-benzimidazole-1-carboxylate
• CAS No.: 161468-45-7
• Molecular Formula: C12H14 N2 O3
• Molecular Weight: 234.25
• Hs Code.: 29225090
• European Community (EC) Number: 809-065-7
• DSSTox Substance ID: DTXSID00373201
• Nikkaji Number: J1.483.204A
• Wikidata: Q82161367
• Mol file: 161468-45-7.mol

Synonyms:161468-45-7;tert-butyl 2-oxo-3H-benzimidazole-1-carboxylate;2-Hydroxy-benzoimidazole-1-carboxylic acid tert-butyl ester;tert-butyl 2-oxo-2,3-dihydro-1H-benzimidazole-1-carboxylate;tert-Butyl 2-hydroxy-1H-benzo[d]imidazole-1-carboxylate;1H-Benzimidazole-1-carboxylic acid, 2,3-dihydro-2-oxo-, 1,1-dimethylethyl ester;tert-Butyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-1-carboxylate;2-Oxo-2,3-dihydrobenzimidazole-1-carboxylic Acid tert-Butyl Ester;N-Boc-2-hydroxybenzimidazole;SCHEMBL2256797;DTXSID00373201;GMUWCTKADZFKLT-UHFFFAOYSA-N;MFCD02179636;AKOS022181860;AKOS037629349;AS-54984;CS-0120607;W11776;A911361;1-(tert-Butoxycarbonyl)-1H-benzimidazole-2(3H)-one;tert-Butyl2-hydroxy-1H-benzo[d]imidazole-1-carboxylate;2-Hydroxybenzoimidazole-1-carboxylic acid tert-butyl ester;2-Oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester;2,3-dihydro-2-oxo-1h-benzimidazole-1-carboxylic acid tert-butyl ester;2-Hydroxy-benzoimidazole-1-carboxylic acid tert-butyl ester, AldrichCPR;1h-benzimidazole-1-carboxylic acid,2,3-dihydro-2-oxo-,1,1-dimethylethyl ester;2,3-dihydro-2-oxo-1H-benzimidazole-1-carboxylic acid, 1,1-dimethylethyl ester

Chemical Property of tert-butyl 2-oxo-3H-benzimidazole-1-carboxylate

Chemical Property:

• PSA: 64.35000
• LogP: 2.52510
• Storage Temp.: Store at 0-5°C
• Solubility.: D?M, Ethyl Acetate
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 234.10044231
• Heavy Atom Count: 17
• Complexity: 335

Purity/Quality:

98%min ^*data from raw suppliers

N-Boc-2-hydroxybenzimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C2=CC=CC=C2NC1=O
• Uses: 2-Oxo-2,3-dihydrobenzimidazole-1-carboxylic Acid tert-Butyl Ester is an substituent in the synthesis of Domperidone (D531100), a novel peripheral dopamine receptor antagonist that does not cross the blood-brain barrier and is used as an anti-emetic agent.

Technology Process of tert-butyl 2-oxo-3H-benzimidazole-1-carboxylate

There total 3 articles about tert-butyl 2-oxo-3H-benzimidazole-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

1,3-dihydro-2H-benzimidazol-2-one (615-16-7) + 2,3-Dihydro-2-oxo-1H-benzimidazole-1,3-(2H)-dicarboxylic acid bis(1,1-dimethylethyl ester) (161468-58-2) → tert‐butyl 2‐oxo‐2,3‐dihydro‐1H‐benzo[d]imidazole‐1‐carboxylate (161468-45-7)

Guidance literature:

With potassium carbonate; In acetonitrile; Heating;

DOI:10.1021/jo00111a014

Reference yield: 89.0%

1,3-dihydro-2H-benzimidazol-2-one (615-16-7) + di-tert-butyl dicarbonate (24424-99-5) → tert‐butyl 2‐oxo‐2,3‐dihydro‐1H‐benzo[d]imidazole‐1‐carboxylate (161468-45-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 10h;

DOI:10.1016/j.bmcl.2009.02.008

Reference yield:

1,2-diamino-benzene (95-54-5) → tert‐butyl 2‐oxo‐2,3‐dihydro‐1H‐benzo[d]imidazole‐1‐carboxylate (161468-45-7)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid

2: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere

With sodium hydride; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/bc500509a

upstream raw materials:

1,3-dihydro-2H-benzimidazol-2-one

di-tert-butyl dicarbonate

2,3-Dihydro-2-oxo-1H-benzimidazole-1,3-(2H)-dicarboxylic acid bis(1,1-dimethylethyl ester)

1,2-diamino-benzene

Downstream raw materials:

2,3-dihydro-2-oxo-3-(4-tolylsulfonyl)-1H-benzimidazole-1-carboxylic acid 1,1-dimethylethyl ester

1-(4-nitrobenzenesulfonyl)-1,3-dihydrobenzimidazol-2-one

Refernces

• 1、 Bertinaria, Massimo,Blua, Federica,Boscaro, Valentina,Gallicchio, Margherita,Gastaldi, Simone,Gianquinto, Eleonora,Giorgis, Marta,Macdonald, Justin A.,Marini, Elisabetta,Sandall, Christina F.,Spyrakis, Francesca. "Chemical modulation of the 1-(Piperidin-4-yl)-1,3-dihydro-2h-benzo[d]imidazole-2-one scaffold as a novel NLRP3 inhibitor". . . Retrieved 2021/07/13.
• 2、 Abbas, Muhammad Azhar,Hameed, Shahid,Farman, Muhammad,Kressler, J?rg,Mahmood, Nasir. "Conjugates of degraded and oxidized hydroxyethyl starch and sulfonylureas: Synthesis, characterization, and in vivo antidiabetic activity". . p. 120 - 127. Retrieved 2015/01/30.