Sulfuric Acid → N-ethyl-N-(2,2,2-trifluoroethyl)aniline

HRID 2071868Notes

Reaction equation

HRID 2071868 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].S(C1C=CC(C)=CC=1)(O[CH2:20][C:21]([F:24])([F:23])[F:22])(=O)=O.S(=O)(=O)(O)O>O>[CH2:1]([N:3]([CH2:20][C:21]([F:24])([F:23])[F:22])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7670N-EthylanilineHCID 10340Sodium CarbonateHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)

Product 1

HCID 13510111N-ethyl-N-(2,2,2-trifluoroethyl)aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

484 parts of N-ethylaniline, 106 parts of sodium carbonate and 254 parts of 2,2,2-trifluoro-ethyl tosylate are heated for 48 hours at 190°-200° C. The cooled reaction mixture is diluted with 1000 parts by volume of distilled water and acidified with sulphuric acid until it is distinctly acid to Congo red paper. The N-ethyl-N-(2,2,2-trifluoro-ethyl)-aniline which is formed is then steam distilled. The lower organic layer of the distillate is separated and subjected to distillation under reduced pressure. 182 parts of N-ethyl-N-(2,2,2-trifluoro-ethyl)-aniline are thus obtained, distilling at 53°-54° C. under 1 mm of mercury, of which the elementary analysis is as follows:

Workup

  1. customThe cooled reaction mixture

Sources & evidence

ORD record
ord-b224e815a997461ea04dd9ce7e692be9
Source dataset
uspto-grants-1977_09
Patent number
US04049375

Reaction notes

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