1-Propanethiol, 2-amino- → 3(R,S)-methyl-7-sulfamoyl-3,4-dihydrothieno[3,2-f]-1,4-thiazepin-5(2H)-one

HRID 1197431Notes

Reaction equation

HRID 1197431 reaction equation
CC(C)([O-])C.[K+].[NH2:7][CH:8]([CH3:11])[CH2:9][SH:10].Cl[C:13]1[S:14][C:15]([S:23](=[O:26])(=[O:25])[NH2:24])=[CH:16][C:17]=1[C:18](OCC)=[O:19]>C(O)C>[CH3:11][CH:8]1[NH:7][C:18](=[O:19])[C:17]2[CH:16]=[C:15]([S:23](=[O:25])(=[O:26])[NH2:24])[S:14][C:13]=2[S:10][CH2:9]1

Participants

5

Reactant 3

HCID 1658451-Propanethiol, 2-amino-HCID 19106450Ethyl 2-chloro-5-sulfamoylthiophene-3-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 191064643(R,S)-methyl-7-sulfamoyl-3,4-dihydrothieno[3,2-f]-1,4-thiazepin-5(2H)-oneYield 72.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of potassium tert-butoxide (8.56 g, 0.076 mol) in ethanol (75 mL) was added 2(R,S)-aminopropanethiol (3.1 g, 0.0246 mol) and ethyl 2-chloro-5-sulfamoylthiophene-3-carboxylate (5.98 g, 0.022 mol). The mixture was heated at reflux for 24 hours, and then allowed to stand at room temperature for 24 hours. Following removal of most of the solvent by vacuum concentration, the mixture was acidified to pH 3 with dilute hydrochloric acid. The resulting solids were removed by filtration and dried to give 4.44 g of the title compound, mp 184°-187° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 hours
  3. customremoval of most of the solvent
  4. concentrationby vacuum concentration
  5. customThe resulting solids were removed by filtration
  6. customdried

Sources & evidence

ORD record
ord-010f263d5e2e4fe6933dd53dea498f88
Source dataset
uspto-grants-1994_01
Patent number
US05276025

Reaction notes

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