3,5-Dichloroaniline → HCID 23333926, compound

HRID 2049534Notes

Reaction equation

HRID 2049534 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2].[Cl:13][C:14]1[CH:15]=[C:16]([CH:18]=[C:19]([Cl:21])[CH:20]=1)[NH2:17]>C(O)C>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[N:17][C:16]2[CH:15]=[C:14]([Cl:13])[CH:20]=[C:19]([Cl:21])[CH:18]=2)=[CH:7][CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 122813,5-DichloroanilineHCID 15294Methyl 4-Formylbenzoate

Product 1

HCID 23333926HCID 23333926, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-Carbomethoxybenzaldehyde (0.20 moles) was treated with 3,5-dichloroaniline (0.20 moles) with vigorous stirring in a 1 liter Erlenmeyer Flask. After 15 mins., 33 cc. of 95% ethanol was added and the reaction mixture was stirred vigorously for an additional 5 minutes. The reaction mixture was left standing at room temperature for 10 min.; then it was placed in an ice bath for 0.5 hours. The crystals which formed were collected, washed with 95% ethanol, and air-dried. Recrystallization from 85% ethanol gave N-(p-carbomethoxybenzylidene)-3,5-dichloroaniline.

Workup

  1. stirringthe reaction mixture was stirred vigorously for an additional 5 minutes
  2. waitThe reaction mixture was left
  3. waitstanding at room temperature for 10 min.
  4. waitthen it was placed in an ice bath for 0.5 hours
  5. customThe crystals which formed
  6. customwere collected
  7. washwashed with 95% ethanol
  8. customair-dried
  9. customRecrystallization from 85% ethanol

Sources & evidence

ORD record
ord-db8358dd48d54bedb37ca7cd87388895
Source dataset
uspto-grants-1980_04
Patent number
US04198349

Reaction notes

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