Methyl iodide → 4-(Methylsulfanyl)-2-(trifluoromethyl)aniline

HRID 1759598Notes

Reaction equation

[S:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1)[C:2]#N.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].CI.CCCCCC>C(O)C.O>[CH3:2][S:1][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([C:11]([F:12])([F:13])[F:14])[CH:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 4-thiocyano-2-trifluoromethylaniline (2.1 g., 0.01 mole) in ethanol (25 ml) is added to a stirred solution of sodium sulfide nonahydrate (2.4 g., 0.01 mole) in water (5 ml) and the mixture is warmed (50° C.) for 40 minutes. Methyl iodide (1.55 g., 0.011 mole) is added to the warm reaction all at once, and stirring is continued for two hours. Thin layer chromatography on silica gel with 50 percent hexane-50 percent methylene chloride diluent alongside an authentic sample shows that all of the thiocyano compound is reacted to produce the desired product.

Workup

customis reacted

Sources & evidence

ORD record: ord-0bc0d84c7a224e5997ba3cdbbed626cb
Source dataset: uspto-grants-1982_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04341901

Reaction notes

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