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

HRID 6553

Reaction equation

HRID 6553 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): δ 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-6b77fd970be54f8dbe3fb67395b6565b
Source dataset
uspto-grants-1993_09
Patent number
US05248777

Linked notes

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