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

HRID 2254089Notes

Reaction equation

HRID 2254089 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>O1CCCC1>[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 tetrahydrofuran (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 stood at room temperature for 2 hours and was 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.

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-1667bc685d9f4a489a6962467a86ce5d
Source dataset
uspto-grants-1993_08
Patent number
US05234926

Reaction notes

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