Water → HCID 86615234, compound

HRID 2244359Notes

Reaction equation

HRID 2244359 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[O:4].[C:17](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[N:10]([CH3:17])[C:11](=[O:16])[C:12]([F:13])([F:14])[F:15])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2805185Methyl 3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate

Product 1

HCID 86615234HCID 86615234, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2 g of 3-(2,2,2-trifluoro-acetylamino)-thiophene-2-carboxylic acid methyl ester (7.9 mmol), 1.31 g of potassium carbonate (9.48 mmol) and 596 μl of methyl iodide (9.48 mmol) in DMF (7.5 ml) was stirred for 2 d. The reaction mixture was then poured into water and extracted with DCM. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to give 2.055 g (97%) of 3-[methyl-(2,2,2-trifluoro-acetyl)-amino]-thiophene-2-carboxylic acid methyl ester as a white solid. MS (ISP) 268.1 (M+H)+.

Workup

  1. extractionextracted with DCM
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0fc6e7eea4324921ad17154d216f60ac
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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