Benzyl mercaptan → HCID 68183090, compound

HRID 513707Notes

Reaction equation

HRID 513707 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH2:15]([SH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>CCO.O>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([S:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 10340Sodium CarbonateHCID 735797Methyl 4-chloro-3-nitrobenzoate

Product 1

HCID 68183090HCID 68183090, compoundYield 177.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of methyl 4-chloro-3-nitrobenzoate (1 g, 4.65 mmol) in EtOH (13 ml) was added to a solution of benzylmercaptan (0.65 ml, 5.53 mmol), Na2CO3 (0.64 g, 6.1 mmol) and water (3 ml) and the reaction was heated under reflux for 4 h. After cooling, the mixture was diluted with water. The resulting precipitate was collected by filtration, washed with n-hexane and dried to give the title compound (2.5 g, 88%). The structure was confirmed by 1H NMR.

Workup

  1. temperaturethe reaction was heated
  2. temperatureunder reflux for 4 h
  3. temperatureAfter cooling
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with n-hexane
  6. customdried

Sources & evidence

ORD record
ord-4aca2f003c9a46b39b0a2a78c1429e0c
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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