Hydrochloric Acid → 2H,3H-1lambda6-thieno[2,3-d][1,2]thiazole-1,1,3-trione

HRID 2212238Notes

Reaction equation

HRID 2212238 reaction equation
[S:1]([C:5]1[C:6](C(OC)=O)=[CH:7][S:8][CH:9]=1)(=[O:4])(=[O:3])[NH2:2].[CH3:14][O-:15].[Na+].Cl>CO>[O:4]=[S:1]1(=[O:3])[C:5]2[CH:6]=[CH:7][S:8][C:9]=2[C:14](=[O:15])[NH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 30422843-Thiophenecarboxylic acid, 4-(aminosulfonyl)-, methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 140865502H,3H-1lambda6-thieno[2,3-d][1,2]thiazole-1,1,3-trione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-sulfamoylthiophene-3-carboxylate (2.7 g, 12.2 mmol), methanol (12 mL), and a 25% methanolic solution of sodium methylate (3.6 mL) was refluxed for 48 h. The reaction mixture was cooled to room temperature and acidified with concentrated hydrochloride acid, and the precipitated product was collected and washed with water. Recrystallized from water, yielded 400 mg of the title compound. MS: 187.8 (M−1), 189.5 (M+1). 1H NMR (DMSO-d6): 8.34 (d, J=4.4 Hz, 1H), 7.705 (d, J=4.8 Hz, 1H).

Workup

  1. customthe precipitated product was collected
  2. washwashed with water
  3. customRecrystallized from water

Sources & evidence

ORD record
ord-7b537e2b0847459fa2f532f5b070956c
Source dataset
uspto-grants-2006_09
Patent number
US07101880B2

Reaction notes

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