3-Hydroxy-2-(phenylamino)-4-(phenylimino)-2-cyclobuten-1-one → 1-[2-Hydroxy-3-(cis-3,5-dimethyl-4-ethyl-1-piperazinyl)-4-oxo-2-cyclobuten-1-ylidene]-cis-3,5-dimethyl-4-ethylpiperazinium hydroxide

HRID 1390357Notes

Reaction equation

HRID 1390357 reaction equation
[NH:1]([C:8]1[C:9](=[O:20])[C:10](=[N:13][C:14]2[CH:19]=[CH:18]C=CC=2)[C:11]=1[OH:12])[C:2]1[CH:7]=[CH:6]C=CC=1.C[C@H]1CN[CH2:25][C@@H:24]([CH3:28])[N:23]1[CH2:29][CH3:30]>>[OH-:12].[OH:12][C:11]1[C:10](=[N+:13]2[CH2:14][C@H:19]([CH3:18])[N:23]([CH2:29][CH3:30])[C@H:24]([CH3:25])[CH2:28]2)[C:9](=[O:20])[C:8]=1[N:1]1[CH2:2][C@H:7]([CH3:6])[N:1]([CH2:2][CH3:7])[C@H:8]([CH3:9])[CH2:11]1

Participants

3

Reactant 2

HCID 109783293-Hydroxy-2-(phenylamino)-4-(phenylimino)-2-cyclobuten-1-oneHCID 28363792(2R,6S)-1-ethyl-2,6-dimethylpiperazine

Product 1

HCID 867362921-[2-Hydroxy-3-(cis-3,5-dimethyl-4-ethyl-1-piperazinyl)-4-oxo-2-cyclobuten-1-ylidene]-cis-3,5-dimethyl-4-ethylpiperazinium hydroxide

Conditions

Temperature
213 °C

Procedure

A mixture of 1.5 grams of 2-anilino-3-hydroxy-4-(phenylimino)-2-cyclobuten-1-one and 1.2 grams of cis-2,6-dimethyl-1-ethylpiperazine is heated at 213° C. in an atmosphere of dry nitrogen for 10 minutes. It is then mixed thoroughly with 25 ml. of anhydrous ethyl ether and suction filtered and this process is repeated. The solid is then dissolved in 200 ml. of anhydrous ethyl ether at room temperature by stirring for 10 minutes. The solution is then stirred with activated charcoal, filtered, and concentrated to a volume of 25 ml. The solid which forms is separated by filtration to give 1-[2-hydroxy-3-(cis-3,5-dimethyl-4-ethyl-1-piperazinyl)-4-oxo-2-cyclobuten-1-ylidene]-cis-3,5-dimethyl-4-ethylpiperazinium hydroxide inner salt as pale pink crystals melting at about 178°-181° C.

Workup

  1. additionIt is then mixed thoroughly with 25 ml
  2. filtrationof anhydrous ethyl ether and suction filtered
  3. dissolutionThe solid is then dissolved in 200 ml
  4. stirringThe solution is then stirred with activated charcoal
  5. filtrationfiltered
  6. concentrationconcentrated to a volume of 25 ml
  7. customThe solid which forms is separated by filtration

Sources & evidence

ORD record
ord-d781e271b2db400bb092ddb62bc62a95
Source dataset
uspto-grants-1979_02
Patent number
US04138566

Reaction notes

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