Dimethylformamide → N-(2-ethylhexyl)-N-propylaniline

HRID 361271

Reaction equation

HRID 361271 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][CH3:3].[CH2:11]([CH:13]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:14]Br)[CH3:12].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:11]([CH:13]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:14][N:4]([CH2:1][CH2:2][CH3:3])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12153Benzenamine, N-propyl-HCID 868042-Ethylhexyl bromide

Product 1

HCID 53707404N-(2-ethylhexyl)-N-propylanilineYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of N-propylaniline (24 parts), 2-ethylhexyl bromide (58 parts), anhydrous potassium carbonate (42 parts) and dry N,N-dimethylformamide (50 parts) was stirred at 125° C. for 16 hours. The cooled reaction mixture was poured into water (250 parts), the organic phase separated and washed with water (2×200 parts) and dried at 90° C. and 15 mmHg to yield N-(2-ethylhexyl)-N-propylaniline (49 parts, 89%). Acetic anhydride was added to this to make a total of 69.5 parts.

Workup

  1. customThe cooled reaction mixture
  2. customthe organic phase separated
  3. washwashed with water (2×200 parts)
  4. customdried at 90° C.

Sources & evidence

ORD record
ord-e8c4b4af7a854ceba4a19e440aee6972
Source dataset
uspto-grants-1999_02
Patent number
US05865857

Linked notes

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