Sodium Hydroxide → HCID 12496842, compound

HRID 1155308Notes

Reaction equation

HRID 1155308 reaction equation
[CH3:1][C:2]([CH3:24])=[CH:3][CH2:4][CH:5]1[C:9](=[O:10])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:6]1=[O:23].[OH-].[Na+].O.O.O.O.O.O.O.O.O.O.O.O.P([O-])([O-])(O)=[O:40].[Na+].[Na+]>O>[C:11]1([N:8]([C:9](=[O:10])[CH:5]([CH2:4][CH:3]=[C:2]([CH3:24])[CH3:1])[C:6]([OH:23])=[O:40])[NH:7][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 35455FeprazoneHCID 61456Phosphoric acid, disodium salt, dodecahydrate

Product 1

HCID 12496842HCID 12496842, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

103.8 gm (0.324 mol) of 4-(3-methyl-2-butenyl)-1,2-diphenyl-3,5-dioxopyrazolidine were dissolved in a solution of 12.96 gm (0.324 mol) of sodium hydroxide pellets and 57.3 gm (0.16 mol) of disodium hydrogen phosphate dodecahydrate in 400 ml of water. The reaction mixture was heated for 30 hours in an atmosphere of nitrogen, then cooled, diluted with 600 ml of water, and filtered. The filtered solution was neutralized (pH 7 to 7.5) with 2 N hydrochloric acid and extracted several times with chloroform. The combined chloroform extracts were evaporated, leaving crude 2-(3-methyl-2-butenyl)propanedioic acid mono(1,2-diphenylhydrazide) which was dissolved in 500 ml of 10% aqueous ammonium hydroxide. To this solution a solution of 17.9 gm (0.162 mol) of calcium chloride in 50 ml of water was added while stirring.

Workup

  1. temperatureThe reaction mixture was heated for 30 hours in an atmosphere of nitrogen
  2. temperaturecooled
  3. filtrationfiltered
  4. extractionextracted several times with chloroform
  5. customThe combined chloroform extracts were evaporated

Sources & evidence

ORD record
ord-c71ce10a7600448ab11264140972e776
Source dataset
uspto-grants-1981_11
Patent number
US04301177

Reaction notes

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