Sulfuryl chloride → methyl 2-(acetylamino)-5-chloro-3-thiophenecarboxylate

HRID 1973414Notes

Reaction equation

HRID 1973414 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[CH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:3])[CH3:2].S(Cl)([Cl:17])(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:1]([NH:4][C:5]1[S:6][C:7]([Cl:17])=[CH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 2808565Methyl 2-acetamidothiophene-3-carboxylate

Product 1

HCID 818981methyl 2-(acetylamino)-5-chloro-3-thiophenecarboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 19.9 parts of methyl 2-acetamidothiophene-3-carboxylate in 200 parts by volume of chloroform, 8.2 parts by volume of sulfuryl chloride is added dropwise at below 30° C. The mixture is stirred at room temperature for 30 minutes and then cooled with ice. To the mixture, about 300 parts by volume of saturated aqueous sodium bicarbonate solution is cautiously added with stirring. The chloroform layer is separated, washed with water and dried over sodium sulfate. Evaporation of the solvent gives methyl 2-acetamido-5-chlorothiophene-3-carboxylate as crystals. Recrystallization from methanol gives needles melting at 110°-110.5° C. This compound is identical with that obtained in Reference Example 17.

Workup

  1. temperaturecooled with ice
  2. stirringwith stirring
  3. customThe chloroform layer is separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-df3983827b9840ff936257e6925977ae
Source dataset
uspto-grants-1976_12
Patent number
US03997545

Reaction notes

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