Benzyl mercaptan → HCID 12070491, compound

HRID 990262Notes

Reaction equation

HRID 990262 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=O)=[CH:5][CH:4]=1.[CH2:14]([SH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:23]>C1(C)C=CC=CC=1>[CH2:14]([S:21][C:7](=[S:23])[C:6]1[CH:10]=[CH:11][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 99664-(Trifluoromethyl)benzoic acidHCID 14817Phosphorus sulfide (P2S5)

Product 1

HCID 12070491HCID 12070491, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-trifluoromethylbenzoic acid (1.90 g), benzyl mercaptan (1.24 g) and phosphorus pentasulfide (4.44 g) in toluene (40 ml) was refluxed for 10 h. A dark red color was developed immediately after heating. After the reaction was complete (as monitored by GC-MS), it was cooled to room temperature and purified by a column chromatography packed with neutral alumina, eluting with benzene. Removal of the solvent by distillation gave the single compound, benzyl-4-trifluoromethyidithiobenzoate (2.30 g, 74%). It was further characterized by 1H and 13C-NMR.

Workup

  1. temperaturewas refluxed for 10 h
  2. temperatureafter heating
  3. custompurified by a column chromatography
  4. washeluting with benzene
  5. customRemoval of the solvent
  6. distillationby distillation

Sources & evidence

ORD record
ord-363f500e78164c27b6a2c2d1b295a838
Source dataset
uspto-grants-2002_10
Patent number
US06458968B2

Reaction notes

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