Acetone → Methyl 3-[2-(acetylsulfanyl)acetamido]benzoate

HRID 839623Notes

Reaction equation

HRID 839623 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:4].[S:16]1C=CC=C1CC([O-])=O.[K+].[CH3:26][C:27](C)=[O:28]>CCCCCC>[C:27]([S:16][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:4])(=[O:28])[CH3:26]

Participants

5

Reactant 3

HCID 180AcetoneHCID 2304955methyl 3-[(chloroacetyl)amino]benzoateHCID 23696799Potassium 2-thienylacetate

Product 1

HCID 20382891Methyl 3-[2-(acetylsulfanyl)acetamido]benzoate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of methyl 3-(2-chloroacetamido)benzoate (16 g., 0.07 mole) and potassium thiolacetate (7.1 g., 0.065 mole) in 150 ml. of acetone is refluxed for 4.5 hr. After cooling, the reaction mixture is filtered and the filtrate concentrated under reduced pressure. The residual solid thus obtained is slurried with n-hexane to afford an 86% yield of crude product. Crystallization of the crude product from ethyl acetate-n-hexane affords analytically pure METHYL 3-[2-(ACETYLTHIO)ACETAMIDO]BENZOATE, m.p. 117.5°-119.5° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture is filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residual solid thus obtained
  5. customto afford an 86% yield of crude product
  6. customCrystallization of the crude product from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-7d475b2e85cb4ee6a37befc20f1046a7
Source dataset
uspto-grants-1978_06
Patent number
US04096277

Reaction notes

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