Organic Process Research & Development
ARTICLE
for 2 h under a nitrogen atmosphere. Following cooling on an ice
bath for 30 min, the reaction mixture was filtered, and the residue
was rinsed with IPA (2 Â 20 mL). The residue was dried under
vacuum at 90 °C for 16 h to give 9 as a pale-brown solid (64.5 g,
85%); νmax/cmÀ1 3402, 3333, 1563, 1516, 1454, 1361; δH
(300 MHz, DMSO-d6) 5.83 (2H, br s, NH2), 6.45 (1H, d, J 5.4,
ArH), 6.98 (1H, d, J 5.4, ArH); δC (75.5 MHz, DMSO-d6)
114.2 (C), 120.6, 124.1 (2 Â CH), 148.0, 168.3 (2 Â C);
HRMS (ES+): Exact mass calculated for C5H6NO2S [(M +
H)+ À HCl], 144.0119. Found 144.0112; m/z (ES+) 143.9
{[(M + H)+ À HCl], 28%}.
’ ACKNOWLEDGMENT
Enterprise Ireland is acknowledged for financial support for O.
McN. and M.K. During the course of this work, helpful discussion
with Dr. Sarah O’Keeffe, Mr. Richard D. Spencer, Dr. Mark
LaPack, Dr. Alfeo Borghese, and Dr. Tony Y. Zhang is appreciated.
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was added dropwise over 20 min at 0 °C. A brown solid
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min and filtered to give 2 HCl as a brown solid (95.2 g, 77%).
3
(Found C, 48.69; H, 4.16; N, 5.15. C10H9NSCl2 requires C,
48.79; H, 3.69; N, 5.69%); νmax/cmÀ1 3419, 1670, 1488; δH
(300 MHz, DMSO-d6) 7.19 (1H, d, J 5.4, ArH), 7.57 (2H, d,
J 8.7, ArH), 7.67À7.71 (3H, 2 Â overlapping d, J 8.7, 5.4, ArH);
δC (150 MHz, DMSO-d6) 124.8, 126.3 (2 Â CH, ArCH), 127.1,
128.3 (2 Â C, ArC), 129.1, 130.0 (2 Â CH, ArCH), 130.5,
133.0 (2 Â C, ArC); HRMS (ES+): Exact mass calculated for
C10H9NSCl [(M + H)+ À HCl], 210.0144. Found 210.0135; m/
z (ES+) 210.0 {[(M + H)+ À HCl], 18%}.
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’ ASSOCIATED CONTENT
S
Supporting Information. Characterization data for the
b
HCl salt of 2. This material is available free of charge via the
’ AUTHOR INFORMATION
Corresponding Author
*dmit@lilly.com.
985
dx.doi.org/10.1021/op200030t |Org. Process Res. Dev. 2011, 15, 981–985