4-Chloro-2-toluidine → HCID 178428210, compound

HRID 268275Notes

Reaction equation

HRID 268275 reaction equation
Cl.N([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]3[N:21]=[CH:20][NH:19][C:17]3=2)[N:12]=[C:11]([CH3:22])[CH:10]=1)C1C=CC=CC=1.[Cl:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[C:26]([CH3:31])[CH:25]=1>CN(C)C=O>[ClH:23].[Cl:23][C:24]1[CH:30]=[CH:29][C:27]([NH:28][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]4[N:21]=[CH:20][NH:19][C:17]4=3)[N:12]=[C:11]([CH3:22])[CH:10]=2)=[C:26]([CH3:31])[CH:25]=1

Participants

4

Reactant 2

HCID 72514-Chloro-2-toluidineHCID 178428198HCID 178428198, compound

Product 1

HCID 178428210HCID 178428210, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 22 g. (0.1 m.) of the compound of Example I, C. and 14 g. (0.1 m.) of 4-chloro-2-methylaniline in 200 ml. of dimethylformamide was heated under reflux for 17 hours and filtered hot. The crystalline product which separated on cooling was filtered, washed with cold dimethylformamide, then ether and air-dried, giving 22 g. of straw-colored product. Recrystallization from 550 ml. of ethanol gave 14 g. m.p. 199°-206°.

Workup

  1. temperatureunder reflux for 17 hours
  2. filtrationfiltered hot
  3. customThe crystalline product which separated
  4. temperatureon cooling
  5. filtrationwas filtered
  6. washwashed with cold dimethylformamide
  7. dry with materialether and air-dried
  8. customgiving 22 g
  9. customRecrystallization from 550 ml
  10. customof ethanol gave 14 g

Sources & evidence

ORD record
ord-54c690e2dd194fad8b727d4de27b0577
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Reaction notes

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