Ammonia → 4-(Trifluoromethylthio)toluene

HRID 1441050Notes

Reaction equation

HRID 1441050 reaction equation
[C:1]1([CH3:8])[CH:6]=[CH:5][C:4]([SH:7])=[CH:3][CH:2]=1.N.[F:10][C:11](I)([F:13])[F:12].C(OCC)C>O>[F:10][C:11]([F:13])([F:12])[S:7][C:4]1[CH:5]=[CH:6][C:1]([CH3:8])=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 78114-MethylbenzenethiolHCID 16843Trifluoroiodomethane

Product 1

HCID 27779084-(Trifluoromethylthio)toluene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

p-Toluenethiol (8 g.) was added to liquid ammonia (60 ml.) at -30°. Trifluoromethyl iodide (18 g.) was added and the mixture was irradiated with uv light (297nm.) for 30 minutes. Dry diethyl ether (35 ml.) was added and irradiation was continued for 1 hour. The mixture was allowed to warm to 20° C. and water was added. The mixture was extracted with diethyl ether and the ethereal extracts were washed with sodium thiosulphate solution and then water. The ethereal extracts were dried over anhydrous magnesium sulphate and evaporated in vacuo. Distillation gave 4-trifluoromethylthiotoluene as a mobile yellow-brown liquid (b.p. 78°-80° C., 16 mm.).

Workup

  1. customthe mixture was irradiated with uv light (297nm.) for 30 minutes
  2. customirradiation
  3. extractionThe mixture was extracted with diethyl ether
  4. washthe ethereal extracts were washed with sodium thiosulphate solution
  5. dry with materialThe ethereal extracts were dried over anhydrous magnesium sulphate
  6. customevaporated in vacuo
  7. distillationDistillation

Sources & evidence

ORD record
ord-bbea154da6fa4b3596c40207b5a40f33
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

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