Aniline → N,N-bis(2,2,2-trifluoroethyl)aniline

HRID 2351253Notes

Reaction equation

HRID 2351253 reaction equation
[C:1](C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.[F:16][C:17]([F:23])([F:22])S([O-])(=O)=O.[F:24][C:25]([F:35])([F:34])[CH2:26][I+]C1C=CC=CC=1.[NH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)Cl>[F:16][C:17]([F:23])([F:22])[CH2:1][N:36]([CH2:26][C:25]([F:35])([F:34])[F:24])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 10993805HCID 10993805, compound

Product 1

HCID 13555627N,N-bis(2,2,2-trifluoroethyl)anilineYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

310 mg (1.49 mmol) of 2,6-di-tert-butyl-4-methylpyridine was added to a solution of 654 mg (1.49 mmol) of (2,2,2-trifluoroethyl)phenyliodonium trifluoromethanesulfonate in 5 ml of methylene chloride in an argon atmosphere at room temperature, and then 46 mg (1.49 mmol of aniline was added to the mixture. After stirring for 2 hours at room temperature for 2 hours, the mixture was worked up in the same manner as described in Reference Example 4 to obtain 119 mg (94%) of N,N-bis(2,2,2-trifluoroethyl)aniline.

Sources & evidence

ORD record
ord-b14275546c9940b580cbe384848866a2
Source dataset
uspto-grants-1989_10
Patent number
US04873027

Reaction notes

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