2-Chloro-5-methylaniline → HCID 178425400, compound

HRID 268242

Reaction equation

HRID 268242 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:28]([CH3:31])=[CH:27][C:25]=1[NH2:26]>C(O)C>[ClH:23].[Cl:23][C:24]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:25]=1[NH:26][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

Participants

4

Reactant 2

HCID 667702-Chloro-5-methylanilineHCID 178428198HCID 178428198, compound

Product 1

HCID 178425400HCID 178425400, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 40 g. (0.184 m.) of the compound of Example I, C., 26.1 g. (0.184 m.) of 2-chloro-5-methylaniline and 500 ml. of ethanol was refluxed with stirring overnight. The reaction mixture was concentrated to dryness in vacuo, and the residue dissolved in 700 m. of MeOH. The insolubles were removed by filtration and the MeOh filtrate concentrated in vacuo to give 24 g. m.p. decomposes 315°-400°C. The crude product was triturated in 500 ml. of MeOH, then oven-dried (100°C) to give m.p. 332°-335°C.

Workup

  1. additionA mixture of 40 g
  2. concentrationThe reaction mixture was concentrated to dryness in vacuo
  3. dissolutionthe residue dissolved in 700 m
  4. customThe insolubles were removed by filtration
  5. concentrationthe MeOh filtrate concentrated in vacuo
  6. customto give 24 g
  7. customdecomposes 315°-400°C
  8. customThe crude product was triturated in 500 ml
  9. dry with materialof MeOH, then oven-dried (100°C)
  10. customto give m.p. 332°-335°C.

Sources & evidence

ORD record
ord-95bae04fd6d140d19cd347511d757773
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Linked notes

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