Benzoic acid, 2-mercapto-, methyl ester → 52947-34-9

HRID 1438693Notes

Reaction equation

HRID 1438693 reaction equation
[Na].[C:2]([O:11]C)(=O)[C:3]1[C:4](=[CH:6][CH:7]=[CH:8][CH:9]=1)[SH:5].Cl.Cl[CH2:15][C:16](=[NH:20])[O:17][CH2:18]C>CO>[OH:11][C:2]1[C:3]2[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=2[S:5][C:15]=1[C:16](=[NH:20])[O:17][CH3:18]

Participants

5

Reactant 3

HCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 5360545SodiumHCID 12470659Ethyl 2-chloroethanecarboximidate hydrochloride

Product 1

HCID 304079852947-34-9

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 23 g (1 mol) of sodium in 1 l of anhydrous methanol is mixed with 84 g (0.5 mol) of methyl thiosalicylate while stirring. This is then mixed with 79 g (0.5 mol) of ethyl chloro-acetimidate hydrochloride and heated under reflux for 10 hours. The sodium chloride precipitate is filtered off and the desired product isolated by evaporation (yield: 73 g, m.p. 201° C).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 10 hours
  3. filtrationThe sodium chloride precipitate is filtered off

Sources & evidence

ORD record
ord-32a4ae0098f5414abecf0749eef35871
Source dataset
uspto-grants-1977_11
Patent number
US04056526

Reaction notes

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