Hydrochloric Acid → HCID 10978507, compound

HRID 1419733Notes

Reaction equation

HRID 1419733 reaction equation
C([NH:5][S:6]([C:9]1[S:10][C:11]([Cl:17])=[CH:12][C:13]=1[C:14]([OH:16])=[O:15])(=[O:8])=[O:7])(C)(C)C.Cl.[CH2:19](O)[CH3:20]>>[Cl:17][C:11]1[S:10][C:9]([S:6](=[O:7])(=[O:8])[NH2:5])=[C:13]([C:14]([O:16][CH2:19][CH3:20])=[O:15])[CH:12]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 104473715-Chloro-2-[[(1,1-dimethylethyl)amino]sulfonyl]-3-thiophenecarboxylic acid

Product 1

HCID 10978507HCID 10978507, compoundYield 96%

Procedure

A solution of 2-(N-tert-butylsulfamoyl)-5-chlorothiophene-3-carboxylic acid (60.0 g; 0.201 mol) made by the procedure described by B. Unterhalt and S. Moghaddam, Pharmazie 49, 115-117 (1994) in 700 ml of abs. ethanol saturated with hydrogen chloride was heated with stirring at reflux for 17 h. The cooled solution was evaporated to dryness and the residue was purified by trituration with water and dried to give 52.3 g (96%) of the title compound; 1H-NMR (DMSO-d6): δ 1.31 (t, J=7 Hz, 3H, CH3), 4.32 (q, J=7 Hz, 2H, CH2), 7.55 (s, 1H), 7.77 (br. s, 2H, NH2).

Workup

  1. temperatureat reflux for 17 h
  2. customThe cooled solution was evaporated to dryness
  3. customthe residue was purified by trituration with water
  4. customdried

Sources & evidence

ORD record
ord-fc53bf48f1df43e9aa8a6051855c7a4c
Source dataset
uspto-grants-1999_03
Patent number
US05889002

Reaction notes

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