Formic Acid → Methyl 3-Formamidyl-2-methyl-4-methylsulfanylbenzoate

HRID 1263402Notes

Reaction equation

HRID 1263402 reaction equation
[NH2:1][C:2]1[C:3]([CH3:14])=[C:4]([CH:9]=[CH:10][C:11]=1[S:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[CH:15](O)=[O:16]>C(OC(=O)C)(=O)C>[CH:15]([NH:1][C:2]1[C:3]([CH3:14])=[C:4]([CH:9]=[CH:10][C:11]=1[S:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6])=[O:16]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 18616042Methyl 3-amino-2-methyl-4-methylsulfanylbenzoate

Product 1

HCID 86758893Methyl 3-Formamidyl-2-methyl-4-methylsulfanylbenzoate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

At 40° C., 4.75 g of methyl 3-amino-2-methyl-4-methylsulfanylbenzoate (0.05 mol) were added a little at a time to a mixture of 30 ml of acetic anhydride and 2.2 g of formic acid (0.05 mol). After 5 h, the solution was allowed to cool and poured into ice-water, and the mixture was extracted exhaustively with methylene chloride. The organic phases were washed and dried, and the solvent was subsequently removed. Yield: 4.7 g (0.044 mol).

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted exhaustively with methylene chloride
  3. washThe organic phases were washed
  4. customdried
  5. customthe solvent was subsequently removed

Sources & evidence

ORD record
ord-7c259bcd7d5f46efb7af8313d7eae164
Source dataset
uspto-grants-2003_04
Patent number
US06541423B1

Reaction notes

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