Benzoic acid, 2-mercapto-, methyl ester → HCID 135727378, compound

HRID 2082706Notes

Reaction equation

HRID 2082706 reaction equation
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[Na].Cl.Cl[CH2:15][C:16](=[NH:21])[O:17][CH2:18][CH2:19][CH3:20]>C(O)CC>[OH:10][C:1]1[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[S:4][C:15]=1[C:16](=[NH:21])[O:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 5360545SodiumHCID 20360500HCID 20360500, compound

Product 1

HCID 135727378HCID 135727378, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

16.8 g (0.1 mol) of methyl thiosalicylate are added dropwise to a solution of 4.6 g (0.2 mol) of sodium in 400 ml of anhydrous n-propanol. To this mixture 17.2 g (0.1 mol) of propyl chloroacetimidate hydrochloride are slowly added and the resultant mixture is heated under reflux for 6 hours. The reaction mixture is evaporated under vacuum and the residue distributed between water and dichloromethane. The organic phase is dried, evaporated, and the residue recrystallized from ethyl acetate/diisopropylether solution to yield 6.2 g of yellow crystals with an m.p. of 185° C.

Workup

  1. temperatureunder reflux for 6 hours
  2. customThe reaction mixture is evaporated under vacuum
  3. customThe organic phase is dried
  4. customevaporated
  5. customthe residue recrystallized from ethyl acetate/diisopropylether solution

Sources & evidence

ORD record
ord-ff024ec26d734b218c0b4908a65b6b05
Source dataset
uspto-grants-1978_04
Patent number
US04082770

Reaction notes

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