Water → HCID 18352166, compound

HRID 430832Notes

Reaction equation

HRID 430832 reaction equation
[Br:1][CH:2]([CH2:6][CH2:7][Cl:8])[C:3](Br)=[O:4].[CH3:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[Br:1][CH:2]([CH2:6][CH2:7][Cl:8])[C:3]([N:10]([CH3:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 7515N-MethylanilineHCID 8471TriethylamineHCID 110327461719-99-9

Product 1

HCID 18352166HCID 18352166, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

2-Bromo-4-chlorobutanoyl bromide (80.3 g, 300 mmol) was slowly added to a solution of N-methylaniline (34.5 g, 320 mmol) and triethylamine (33.5 g, 330 mmol) in toluene (340 mL). The reaction was exothermic, and the mixture was cooled to maintain the temperature at about 40° C. After the addition was complete, the resulting thick mixture was stirred for 30 minutes, 150 mL water was added, and the mixture was stirred further. The aqueous and organic phases were separated, and the organic phase was washed with 5% hydrochloric acid and with water. The toluene was evaporated completely under slight vacuum to yield 86.3 g 2-bromo-4-chloro-N-methyl-N-phenylbutanamide (98% yield, approximately 95-96% pure). The triethylamine may be recovered from the aqueous phase by addition of base and separation.

Workup

  1. temperaturethe mixture was cooled
  2. additionAfter the addition
  3. stirringthe mixture was stirred further
  4. customThe aqueous and organic phases were separated
  5. washthe organic phase was washed with 5% hydrochloric acid and with water
  6. customThe toluene was evaporated completely under slight vacuum

Sources & evidence

ORD record
ord-cdd43d3c47e64c4fad48ca61d93fb0ad
Source dataset
uspto-grants-2001_11
Patent number
US06323344B1

Reaction notes

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