Methanol → N-(4-chlorobutyl)-4-fluoro-N-(4-fluorophenyl)benzenamine

HRID 1638632Notes

Reaction equation

HRID 1638632 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([N:7]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)=O.B.S(C)C.CO>O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:7]([C:8]1[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=1)[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 6331BoraneHCID 150877884-chloro-N,N-bis(4-fluorophenyl)butanamide

Product 1

HCID 14722551N-(4-chlorobutyl)-4-fluoro-N-(4-fluorophenyl)benzenamineYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and cooled (0° C.) solution of 48 parts of 4-chloro-N,N-bis(4-fluorophenyl)butanamide in 108 parts of tetrahydrofuran were added 240 parts of a solution of borane, compound with thiobismethane, in tetrahydrofuran. After stirring overnight at room temperature, the reaction mixture was decomposed with 160 parts of methanol. After evaporation, the residue was purified by column chromatography over silica gel using a mixture of trichloromethane and petroleum ether (20:80 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 32.5 parts (91.5%) of N-(4-chlorobutyl)-4-fluoro-N-(4-fluorophenyl)benzenamine as a residue (int. 70).

Workup

  1. stirringAfter stirring overnight at room temperature
  2. customAfter evaporation
  3. customthe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and petroleum ether (20:80 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated

Sources & evidence

ORD record
ord-1842f6b09a674fb381a9e4250ddcaed5
Source dataset
uspto-grants-1989_11
Patent number
US04880808

Reaction notes

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