n-(1,3,4-Thiadiazol-2-yl)acetamide

Base Information

• Chemical Name: n-(1,3,4-Thiadiazol-2-yl)acetamide
• CAS No.: 5393-55-5
• Molecular Formula: C4H5N3OS
• Molecular Weight: 143.169
• Hs Code.: 2934999090
• NSC Number: 4729
• UNII: 26F2JM0PP8
• DSSTox Substance ID: DTXSID20202221
• Nikkaji Number: J1.397.954E,J3.439.122J
• Wikidata: Q27254091
• ChEMBL ID: CHEMBL1288808
• Mol file: 5393-55-5.mol

Synonyms:n-(1,3,4-thiadiazol-2-yl)acetamide;5393-55-5;2-Acetylamino-1,3,4-thiadiazole;Acetamide, N-1,3,4-thiadiazol-2-yl-;2-Acetamido-1,3,4-thiadiazole;1,3,4-Thiadiazole, 2-acetamido-;CL 1950675526;X 134;NSC 4729;N-1,3,4-Thiadiazol-2-ylacetamide;BRN 0124968;UNII-26F2JM0PP8;26F2JM0PP8;CHEMBL1288808;5-acetamido-1,3,4-thiadiazole;NSC-4729;4-27-00-08055 (Beilstein Handbook Reference);Acetazolamide Impurity B;BAS 00134373;SCHEMBL564354;1,4-Thiadiazole, 2-acetamido-;DTXSID20202221;NSC4729;BDBM50331836;STL199110;AKOS000525783;ACETAMIDOTHIADIAZOLE [USP IMPURITY];LS-150237;CS-0277457;FT-0675141;ACETAZOLAMIDE IMPURITY B [EP IMPURITY];CL 19506 7-5526;N-[(Z)-1,3,4-Thiadiazole-2-yl]acetimidic acid;Q27254091;Z56871630

Chemical Property of n-(1,3,4-Thiadiazol-2-yl)acetamide

Chemical Property:

• Melting Point: 350 °C
• Boiling Point: °Cat760mmHg
• PKA: 9.62±0.50(Predicted)
• Flash Point: °C
• PSA: 83.12000
• Density: 1.454g/cm³
• LogP: 0.56950
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 143.01533297
• Heavy Atom Count: 9
• Complexity: 118

Purity/Quality:

99% ^*data from raw suppliers

N-1,3,4-Thiadiazol-2-ylacetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=NN=CS1
• Uses: N-1,3,4-Thiadiazol-2-ylacetamide is an impurity of Acetazolamide (A161500). Acetazolamide impurity B. N-1,3,4-Thiadiazol-2-ylacetamide is an impurity of Acetazolamide (A161500). Acetazolamide EP Impurity B

Technology Process of n-(1,3,4-Thiadiazol-2-yl)acetamide

There total 11 articles about n-(1,3,4-Thiadiazol-2-yl)acetamide 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: 90.0%

1-ethoxymethylenethiosemicarbazide + acetic anhydride (108-24-7) → 2-acetylamino-1,3,4-thiadiazole (5393-55-5)

Guidance literature:

at 90 ℃; for 1h; Heating;

DOI:10.1080/10426500701407755

Reference yield: 83.7%

5,5'-diacetamido-3,3'-diacetyl-2,2'-bi[1,3,4]thiadiazoline → 2-acetylamino-1,3,4-thiadiazole (5393-55-5)

Guidance literature:

With [bis(acetoxy)iodo]benzene; In methanol; for 120h;

DOI:10.3987/COM-04-10137

Reference yield: 76.0%

[1,3,4]Thiadiazol-2-ylamin (4005-51-0) + acetic anhydride (108-24-7) → 2-acetylamino-1,3,4-thiadiazole (5393-55-5)

Guidance literature:

at 100 ℃; for 1.5h;

DOI:10.1007/s11176-006-0022-2

upstream raw materials:

1-ethoxymethylene thiosemicarbazide

acetic anhydride

1-formylthiosemicarbazide

acetyl chloride

Downstream raw materials:

N-(5-bromo-1,3,4-thiadiazol-2-yl)-acetamide

[1,3,4]Thiadiazol-2-ylamin

Refernces

• 1、 Schüttelkopf, Alexander W.,Gros, Ludovic,Blair, David E.,Frearson, Julie A.,Van Aalten, Daan M.F.,Gilbert, Ian H.. "Acetazolamide-based fungal chitinase inhibitors". experimental part. p. 8334 - 8340. Retrieved 2011/02/28.
• 2、 Larina, Lyudmila I.,Elokhina, Valentina N.,Yaroshenko, Tatyana I.,Nakhmanovich, Anatolii S.,Dolgushin, Gennadii V.. "1H, 13C, 15N and19F NMR study of acetylation products of heterocyclic thiosemicarbazones". . p. 667 - 673. Retrieved 2008/03/14.