Ethanol → HCID 178492596, compound

HRID 268259Notes

Reaction equation

HRID 268259 reaction equation
[ClH:1].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.[CH3:23][O:24][C:25]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:26]=1[NH2:27].C(O)C>>[OH2:24].[ClH:1].[CH3:23][O:24][C:25]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:26]=1[NH:27][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.[CH3:23][O:24][C:25]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:26]=1[NH:27][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.[ClH:1]

Participants

4

Reactant 3

HCID 702EthanolHCID 76132,5-DimethoxyanilineHCID 178428198HCID 178428198, compound

Product 1

HCID 178492596HCID 178492596, compound

Procedure

A mixture of 40 g. (0.184 m.) of the compound of Example I, C., 282 g. (0.184 m.) of 2,5-dimethoxyaniline and 500 ml. of ethanol was heated at reflux with stirring overnight. The reaction was concentrated to dryness in vacuo. The product was recrystallized from 800 ml. of MeOH, to give 28 m.p. 258°-293°C. A second recrystallization from 1000 ml. of MeOH gave m.p. 257°-260°C.

Workup

  1. additionA mixture of 40 g
  2. temperatureat reflux
  3. concentrationThe reaction was concentrated to dryness in vacuo
  4. customThe product was recrystallized from 800 ml
  5. customof MeOH, to give 28 m
  6. custom258°-293°C
  7. customA second recrystallization from 1000 ml
  8. customof MeOH gave m.p. 257°-260°C.

Sources & evidence

ORD record
ord-457f7c366ff64050bad93c547817cb8f
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Reaction notes

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