4-Bromoaniline → 2-Butenamide, N-(4-bromophenyl)-3-methyl-

HRID 862267Notes

Reaction equation

HRID 862267 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4](Cl)=[O:5].[Br:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.CCCCCC>C1COCC1>[Br:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][C:4](=[O:5])[CH:3]=[C:2]([CH3:7])[CH3:1])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 8058HexaneHCID 1023943-Methyl-2-butenoyl chloride

Product 1

HCID 5320952-Butenamide, N-(4-bromophenyl)-3-methyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 9.48 g (80 mmol) of 3,3-dimethylacryloyl chloride in 200 ml of dry THF was added with vigorous shaking a solution of 13.76 g (80 mmol) of 4-bromoaniline in 300 ml of dry THF. The mixture was stood at room temperature for 2 h and then treated with 80 g of ice followed by 200 ml of hexane. The organic layer was separated and the aqueous layer was extracted with 2×50 ml of hexanes. The organic layers were combined and washed successively with 30 ml of water and 2×30 ml of saturated NaCl solution and then dried (MgSO4). The solvent was removed in vacuo and the residue purified by recrystallization from an ethyl acetate and hexanes mixture to give the title compound as colorless crystals. PMR (CDCl3): & 1.91 (3H, s), 2.23 (3H, s), 5.73 (1H, broad s), 7.38-7.55 (5H, m).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with 2×50 ml of hexanes
  3. washwashed successively with 30 ml of water and 2×30 ml of saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customthe residue purified by recrystallization from an ethyl acetate and hexanes mixture

Sources & evidence

ORD record
ord-8c738b8c0df44c0a8e66c96c08f626c2
Source dataset
uspto-grants-1998_02
Patent number
US05717094

Reaction notes

Loading…