Triethylamine → N-(4-Bromophenyl)-N-methyl-3-methyl-2-butenamide

HRID 841630Notes

Reaction equation

HRID 841630 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4](Cl)=[O:5].[Br:8][C:9]1[CH:16]=[CH:15][C:12]([NH:13][CH3:14])=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl>[Br:8][C:9]1[CH:16]=[CH:15][C:12]([N:13]([CH3:14])[C:4](=[O:5])[CH:3]=[C:2]([CH3:7])[CH3:1])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1023943-Methyl-2-butenoyl chlorideHCID 2757052Benzenamine, 4-bromo-N-methyl-

Product 1

HCID 22568913N-(4-Bromophenyl)-N-methyl-3-methyl-2-butenamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,3-Dimethylacryloyl chloride (3 mL, 27 mmol) was added to a solution of 4-bromo-N-methyl-aniline (4.55 g, 25 mmol) in 150 mL of dichloromethane followed after 5 minutes by triethyl amine (5 mL, 33 mmol). After 2.5 h at ambient temperature, the reaction mixture was washed with water and the organic phase was dried over anhydrous sodium sulfate and evaporated in vacuo to afford the title product as a brown oil in quantitative yield.

Workup

  1. washthe reaction mixture was washed with water
  2. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-d32314d4592d4a20a7585ccfc08b06a4
Source dataset
uspto-grants-2002_04
Patent number
US06369261B1

Reaction notes

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