Water → Trans-N-(4-bromo-2-methylphenyl)-3-ethoxypropenamide

HRID 568355Notes

Reaction equation

HRID 568355 reaction equation
[CH2:1]([O:3]/[CH:4]=[CH:5]/[C:6](Cl)=[O:7])[CH3:2].[Br:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[C:12]([CH3:17])[CH:11]=1.O>N1C=CC=CC=1>[Br:9][C:10]1[CH:16]=[CH:15][C:13]([NH:14][C:6](=[O:7])/[CH:5]=[CH:4]/[O:3][CH2:1][CH3:2])=[C:12]([CH3:17])[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 114234-Bromo-2-methylanilineHCID 53255003-Ethoxyacryloyl chloride

Product 1

HCID 14221021Trans-N-(4-bromo-2-methylphenyl)-3-ethoxypropenamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Trans-3-ethoxypropenoyl chloride (0.74 g) was added at 0° to a stirred solution of 4-bromo-2-methylaniline (0.93 g) in pyridine (10 cm3). After 0.5 hours water (40 cm3) was added, the solid material was filtered off, washed with water (30 cm3) and dried. The product was recrystallised from ethyl acetate to afford trans-N-(4-bromo-2-methylphenyl)-3-ethoxypropenamide, m.p. 163°-164°, (1.3 g).

Workup

  1. filtrationthe solid material was filtered off
  2. washwashed with water (30 cm3)
  3. customdried
  4. customThe product was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-59ac6bb072e24b90ba5395cc648529d7
Source dataset
uspto-grants-1988_03
Patent number
US04728654

Reaction notes

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