Oxyphenbutazone → HCID 20391701, compound

HRID 259177Notes

Reaction equation

HRID 259177 reaction equation
CCCC[CH:5]1[C:10](=[O:11])[N:9]([C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=2)[N:8]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:6]1=[O:7].[C:25](Cl)(=[O:27])[CH3:26]>C(O)(=O)C>[C:19]1([N:8]2[C:6](=[O:7])[CH2:5][C:10](=[O:11])[N:9]2[C:12]2[CH:17]=[CH:16][C:15]([O:18][C:25](=[O:27])[CH3:26])=[CH:14][CH:13]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 4641OxyphenbutazoneHCID 6367Acetyl chloride

Product 1

HCID 20391701HCID 20391701, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

First, 1-Phenyl-2-(4'-acetyloxyphenyl)-3,5-pyrazolidinedione was prepared as follows. Oxyphenbutazone (1.00 g, 3.1 mmole) was suspended in 4 ml of glacial acetic acid and allowed to react with 2 ml of acetyl chloride at room temperature overnight. The solution was concentrated in vacuo at 86° C. to give a white residue (mp 126°-130° C.). The residue was crystallized from chloroformheptane (6:50) with cooling to give 0.81 g (mp 132°-134° C., 71% yield, lit., R. Pfester and F. Hafliger, Helvetica Chemica Acta, 40, 395 (1957) mp 135°-137° C. from methanol) of 1-phenyl-2-(4'acetyloxyphenyl)-3,5-pyrazolidinedione.

Workup

  1. concentrationThe solution was concentrated in vacuo at 86° C.

Sources & evidence

ORD record
ord-34696864707b49bcbef2c1ac9b75d5e7
Source dataset
uspto-grants-1977_07
Patent number
US04036845

Reaction notes

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