3-Chloro-2-methylaniline → N-(o-Chlorobenzylidene)-2-methyl-3-chloroaniline

HRID 261822Notes

Reaction equation

HRID 261822 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[Cl:10][C:11]1[C:12]([CH3:18])=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14]>C(O)C>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[N:14][C:13]1[CH:15]=[CH:16][CH:17]=[C:11]([Cl:10])[C:12]=1[CH3:18]

Participants

4

Reactant 2

HCID 68943-Chloro-2-methylanilineHCID 69962-Chlorobenzaldehyde

Product 1

HCID 13017551N-(o-Chlorobenzylidene)-2-methyl-3-chloroaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

o-Chlorobenzaldehyde (0.20 mole) is treated with 3-chloro-2-methyl aniline (0.20 mole) with vigorous stirring in a 1 l. Erlenmeyer Flask. After 15 mins., 33 cc of 95% ethanol is added and the reaction mixture is stirred vigorously for an additional 5 mins. The reaction mixture is left standing at room temperature for 10 mins., then it is placed in an ice bath for 0.5 hr. The crystals which formed are collected, washed with 95% ethanol, and air dried. Recrystallization from 85% ethanol gives N-(o-Chlorobenzylidene)-2-methyl-3-chloroaniline. m.p. 83°-85° C.

Workup

  1. stirringthe reaction mixture is stirred vigorously for an additional 5 mins
  2. waitThe reaction mixture is left
  3. waitstanding at room temperature for 10 mins
  4. wait, then it is placed in an ice bath for 0.5 hr
  5. customThe crystals which formed
  6. customare collected
  7. washwashed with 95% ethanol, and air
  8. customdried
  9. customRecrystallization from 85% ethanol

Sources & evidence

ORD record
ord-fe57aa19bca24137beed86e2223902c3
Source dataset
uspto-grants-1979_05
Patent number
US04152452

Reaction notes

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