Hydrochloric Acid → 7-sulfamoyl-3,4-dihydrothieno[3,2-f]-1,4-thiazepin-5(2H)-one

HRID 1197428Notes

Reaction equation

HRID 1197428 reaction equation
[Na].[NH2:2][CH2:3][CH2:4][SH:5].Cl[C:7]1[S:11][C:10]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9][C:8]=1[C:16](OCC)=[O:17].Cl>C(O)C>[S:12]([C:10]1[S:11][C:7]2[S:5][CH2:4][CH2:3][NH:2][C:16](=[O:17])[C:8]=2[CH:9]=1)(=[O:14])(=[O:13])[NH2:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6058CysteamineHCID 5360545Sodium2×HCID 19106450Ethyl 2-chloro-5-sulfamoylthiophene-3-carboxylate

Product 1

HCID 191064767-sulfamoyl-3,4-dihydrothieno[3,2-f]-1,4-thiazepin-5(2H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a round bottomed flask were added ethanol (200 mL) followed by solid sodium (1.0 g, 43.5 mmole). After the sodium dissolved, 2-aminoethanethiol was added (1.57 g, 20.4 mmole). The reaction was stirred for approximately 5.0 minutes and 5-chloro-4-carboethoxythiophene-2-sulfonamide (5.0 g, 18.5 mmole) was added. The reaction was heated at reflux for 24 hrs. The cooled reaction mixture was acidified (6.0N HCl) and the solvent was removed under vacuum. The residue was triturated with water and the resulting solid collected: 4.77 g (98%) mp>270° C.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 24 hrs
  3. customThe cooled reaction mixture
  4. customthe solvent was removed under vacuum
  5. customThe residue was triturated with water
  6. customthe resulting solid collected

Sources & evidence

ORD record
ord-92ea9783b6a44c5b87d9308cc48e1c23
Source dataset
uspto-grants-1994_01
Patent number
US05276025

Reaction notes

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