Dimethylformamide → N-butyl-N-(2-methylprop-2-eneyl)aniline

HRID 2258380

Reaction equation

HRID 2258380 reaction equation
[CH2:1]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]([CH3:22])=[CH2:21].CN(C=O)C>C1(C)C=CC=CC=1>[CH2:1]([N:5]([CH2:21][C:20]([CH3:22])=[CH2:19])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 14310N-Butylaniline

Product 1

HCID 54010992N-butyl-N-(2-methylprop-2-eneyl)aniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N-butylaniline (12.35 parts), anhydrous potassium carbonate (17.1 parts), 3-chloro-2-methylpropene (11.24 parts) and DMF (20 parts) was stirred at 90° C. for 8 hours. The cooled mixture was poured into toluene, washed with water (×2), 1N hydrochloric acid (30 parts) and water (×2). The dried organic phase was evaporated to leave N-butyl-N-(2-methylprop-2-eneyl)aniline (14.3 parts).

Workup

  1. washwashed with water (×2), 1N hydrochloric acid (30 parts) and water (×2)
  2. customThe dried organic phase was evaporated

Sources & evidence

ORD record
ord-fbce872db8c94b7daf813f5029f98905
Source dataset
uspto-grants-1997_08
Patent number
US05660598

Linked notes

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