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

HRID 986013Notes

Reaction equation

HRID 986013 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-394ff3905f63403b8908904790d9efe6
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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