2-Aminothiophenol → 3,3-Dimethyl-2,3-dihydro-5-phenyl-1,5-benzothiazepin-4-one

HRID 609550Notes

Reaction equation

HRID 609550 reaction equation
Br[CH2:2][C:3]([CH3:8])([CH3:7])[C:4](O)=[O:5].[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[SH:16]>>[CH3:7][C:3]1([CH3:8])[C:4](=[O:5])[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16][CH2:2]1

Participants

3

Reactant 2

HCID 87132-AminothiophenolHCID 2719323-Bromo-2,2-dimethylpropanoic acid

Product 1

HCID 195993783,3-Dimethyl-2,3-dihydro-5-phenyl-1,5-benzothiazepin-4-oneYield 71%

Procedure

Bromopivalic acid (Example 10(a)) (59.4 g, 328 mmol) was reacted with 2-aminothiophenol (41 g, 328 mmol, freshly distilled) according to the procedure for Example 1(d). Column chromatography yielded the title compound (52.3 g, 232 mmol, 71%). 1H NMR (DMSO-d6) δ 12.44 (br s, 1H); 7.22 (d, 1H); 6.99 (t, 1H); 6.63 (d, 1H); 6.47 (t, 1H); 5.27 (br s, 2H); 2.88 (s, 2H); 1.14 (s, 6H). MS Da/e=226 (MH+), 208 (M-H2O), 180 (M-CO2). Calcd for C11H15NSO2 : C, 58.64; H, 6.71; N, 6.22; S, 14.23. Found: C, 58.41; H, 6.78; N, 6.13; S, 14.29.

Workup

  1. distillationfreshly distilled)

Sources & evidence

ORD record
ord-5af5d5ac94cd41a39d58ddcdf7d1650f
Source dataset
uspto-grants-1999_12
Patent number
US05998400

Reaction notes

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