Methanol → HCID 178460595, compound

HRID 2371413Notes

Reaction equation

HRID 2371413 reaction equation
C(N([CH2:6][CH3:7])CC)C.C(OC)(=O)C[SH:10].Cl[C:15]1[S:19][C:18]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:17][C:16]=1[N+:24]([O-:26])=[O:25].[P].[S].[CH3:29][OH:30]>O>[CH3:6][CH:7]([C:15]1[S:19][C:18]([S:20](=[O:22])(=[O:21])[NH2:23])=[CH:17][C:16]=1[N+:24]([O-:26])=[O:25])[C:29]([OH:30])=[S:10]

Participants

8

Reactant 6

HCID 887MethanolHCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 27357825-Chloro-4-nitrothiophene-2-sulfonamideHCID 5362487SulfurHCID 5462309Phosphorus

Product 1

HCID 178460595HCID 178460595, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (3.06 ml, 2.22 g, 22 mmol) was added to a stirred mixture of methyl thioglycolate (2.12 g, 20 mmol) and 5-chloro-4-nitrothiophene-2-sulfonamide (4.90 g, 30 mmol) (C. A. Obatemi, Phosphorous and Sulfur, 1982, 13, 119) in methanol (30 ml). After a slight exotherm the reaction mixture became very thick and difficult to stir. The mixture was stirred for an additional 16 hours, then added to water (250 ml). The yellowish solid was collected, washed with water air-dried to yield 5.2 g, mp 153°-154° C. Recrystallization from dichloroethane gave methyl (3-nitro-5-sulfamoylthien-2-yl)thioacetic acid with mp 154°-155° C.

Workup

  1. stirringThe mixture was stirred for an additional 16 hours
  2. customThe yellowish solid was collected
  3. washwashed with water
  4. customair-dried
  5. customto yield 5.2 g, mp 153°-154° C
  6. customRecrystallization from dichloroethane

Sources & evidence

ORD record
ord-980750fcf1f14791b2a8af760e33c1a8
Source dataset
uspto-grants-1992_03
Patent number
US05093332

Reaction notes

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