Chloride → HCID 178428233, compound

HRID 268250Notes

Reaction equation

HRID 268250 reaction equation
[ClH:1].[NH:2]([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)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:23][N:24]([CH3:32])[C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1.C([OH:35])C.[Cl-]>CO>[OH2:35].[ClH:1].[CH3:23][N:24]([CH3:25])[C:6]1[CH:7]=[CH:8][C:3]([NH:2][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)=[CH:4][CH:5]=1.[OH2:35].[OH2:35].[CH3:23][N:24]([C:25]1[CH:31]=[CH:30][C:28]([NH:29][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)=[CH:27][CH:26]=1)[CH3:32].[ClH:1]

Participants

6

Reactant 4

HCID 312ChlorideHCID 702EthanolHCID 7472N,N-dimethyl-p-phenylenediamineHCID 178428198HCID 178428198, compound

Product 1

HCID 178428233HCID 178428233, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 33 g. (0.15 mole) of the compound of Example I, C. and 21 g. (0.15 mole) of p-dimethylaminoaniline in 1800 ml. of ethanol was refluxed overnight. The solvent was removed by evaporation in vacuo. The residue was recrystallized from ethanol to give 32 g. of yellow solid. The solid was dissolved methyl alcohol and was acidified with a saturated etherhydrogen chloride solution. The product was collected as a cream colored solid and was recrystallized from methyl alcohol to give a yellow solid melting at 210°-215° in a yield of 22 g. (42%). Recrystallization from methyl alcohol raised the melting point to 215°-217°.

Workup

  1. additionA mixture of 33 g
  2. customThe solvent was removed by evaporation in vacuo
  3. customThe residue was recrystallized from ethanol
  4. customto give 32 g
  5. customThe product was collected as a cream
  6. customwas recrystallized from methyl alcohol

Sources & evidence

ORD record
ord-2ae844f6825744f397e673a386b9e777
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Reaction notes

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