Benzoic acid, 2-mercapto-, methyl ester → HCID 135897129, compound

HRID 918549Notes

Reaction equation

HRID 918549 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].[C:13]1([NH:19][C:20](=[N:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:21]Cl)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[C:24]1([NH:23][C:20]([C:21]2[S:5][C:4]3[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=3[C:2]=2[OH:11])=[N:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 38572402-chloro-N,N'-diphenylethanimidamideHCID 5360545Sodium

Product 1

HCID 135897129HCID 135897129, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2.3 g (0.1 mol) of sodium in 150 ml of methanol is mixed with 16.8 g (0.1 mol) of methyl thiosalicylate and then a solution of 24.4 g (0.1 mol) of N,N'-diphenyl-2-chloroacetamidine in 250 ml of methanol is added. After heating under reflux for 1 hour, the mixture is poured into ice water and the precipitate filtered and recrystallized from an ethanol/water solution to yield 26.5 g of yellow needles having an m.p. of 152°-153°C.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 1 hour
  3. filtrationthe precipitate filtered
  4. customrecrystallized from an ethanol/water solution

Sources & evidence

ORD record
ord-d559554a9fe2477aa34a4ba08af25527
Source dataset
uspto-grants-1976_07
Patent number
US03971814

Reaction notes

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