Acetyl chloride → HCID 821687, compound

HRID 430518Notes

Reaction equation

HRID 430518 reaction equation
Cl.[NH2:2][C:3]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][S:5][CH:4]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20]>C(Cl)Cl>[C:19]([NH:2][C:3]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][S:5][CH:4]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 2777609Methyl 4-aminothiophene-3-carboxylate Hydrochloride

Product 1

HCID 821687HCID 821687, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 3-aminothiophene-4-carboxylate hydrochloride (3.1 g, 16 mmol) and triethylamine (6.7 mL, 48 mmol), in methylene chloride (75 mL) was stirred 30 minutes and then chilled over wet ice. Acetyl chloride (1.4 mL, 19.2 mmol) was added and the reaction was warmed to ambient temperature and stirred 1 hour. The reaction was quenched with water and diluted with methylene chloride. The phases were separated and the aqueous layer was extracted with methylene chloride. The combined organic layer was washed with water, dried over magnesium sulfate, and concentrated to afford 2.85 g (91%) of methyl 3-acetamidothiophene-4-carboxylate as a brown oil which solidified on standing. The product was suitable for use without purification.

Workup

  1. temperaturechilled over wet ice
  2. customThe reaction was quenched with water
  3. additiondiluted with methylene chloride
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted with methylene chloride
  6. washThe combined organic layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e8fc62634ab34ba0870da39789f20ac8
Source dataset
uspto-grants-2001_11
Patent number
US06323208B1

Reaction notes

Loading…