2,6-Dichloro-1,4-benzenediamine → HCID 13064597, compound

HRID 2198830Notes

Reaction equation

HRID 2198830 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH2:10].[C:11]([NH:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1)(=[O:13])[CH3:12].CO[CH:25](OC)[N:26]([CH3:28])[CH3:27]>C(O)C.CCCCCC>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]=[CH:19][C:18]2[CH:21]=[CH:22][C:15]([NH:14][C:11](=[O:13])[CH3:12])=[CH:16][CH:17]=2)[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]=[CH:25][N:26]([CH3:28])[CH3:27]

Participants

6

Reactant 3

HCID 118602,6-Dichloro-1,4-benzenediamineHCID 739424-AcetamidobenzaldehydeHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 13064597HCID 13064597, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 8058HexaneSolvent

Procedure

A mixture of 3.5 g. of 2,6-dichloro-1,4-phenylenediamine and 3.3 g. of p-acetamidobenzaldehyde in 50 ml. of ethanol is refluxed for 21/2 hours. The reaction mixture is allowed to stand at room temperature for 16 hours, then evaporated in vacuo to give a solid. The solid in 25 ml. of N,N-dimethylformamide dimethylacetal is refluxed for 18 hours. The solvent is evaporated to provide a syrup which is dissolved in ethanol and n-hexane. The addition of more ethanol provides crystals. The crude product is collected, dissolved in 50 ml. of hot ethanol and filtered through diatomaceous earth. The filter is washed with ethanol and n-hexane is added to the filtrate until turbid. The clear liquid is decanted and evaporated in vacuo to give hard, yellow-orange crystals. The material is recrystallized from ethyl acetate/hexane to give 830 mg. of the product of the Example as bright yellow crystals, m.p. 171°-173° C.

Workup

  1. additionA mixture of 3.5 g
  2. customevaporated in vacuo
  3. customto give a solid
  4. customThe solvent is evaporated
  5. customto provide a syrup which
  6. customprovides crystals
  7. customThe crude product is collected
  8. dissolutiondissolved in 50 ml
  9. filtrationof hot ethanol and filtered through diatomaceous earth
  10. washThe filter is washed with ethanol and n-hexane
  11. additionis added to the filtrate until turbid
  12. customThe clear liquid is decanted
  13. customevaporated in vacuo
  14. customto give hard
  15. customThe material is recrystallized from ethyl acetate/hexane
  16. customto give 830 mg

Sources & evidence

ORD record
ord-4648b86718a84ee683b7a8a821eb6924
Source dataset
uspto-grants-1982_11
Patent number
US04360466

Reaction notes

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