Water → 3-chloro-4-(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carboxylic acid

HRID 901955Notes

Reaction equation

HRID 901955 reaction equation
[OH-].[Li+].O.[Cl:4][C:5]1[C:9]([CH2:10][N:11]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH3:12])=[CH:8][S:7][C:6]=1[C:23]([O:25]C)=[O:24]>O1CCOCC1>[Cl:4][C:5]1[C:9]([CH2:10][N:11]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH3:12])=[CH:8][S:7][C:6]=1[C:23]([OH:25])=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 69208322methyl 3-chloro(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carboxylate

Product 1

HCID 692074073-chloro-4-(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carboxylic acidYield 84.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Lithium hydroxide (210 mg, 5.0 mmol) and water (10 ml) were added to a solution of methyl 3-chloro-4-(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carboxylate (990 mg, 2.5 mmol) in dioxan (20 ml) and the mixture stirred for 18 h. The mixture was evaporated and 0.3N potassium hydrogen sulphate was added. The mixture was extracted with ethyl acetate and the organic extracts were washed with water and brine, dried and reduced to afford 3-chloro-4-(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carboxylic acid (800 mg, 84%) as a white solid.

Workup

  1. customThe mixture was evaporated
  2. addition0.3N potassium hydrogen sulphate was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic extracts were washed with water and brine
  5. customdried

Sources & evidence

ORD record
ord-71aa40e6c4c14ecbaeb8ed96d5082c6c
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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