Sodium Hydroxide → HCID 12496842, compound

HRID 1155307Notes

Reaction equation

HRID 1155307 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-:25].[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:25])[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

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 35455Feprazone

Product 1

HCID 12496842HCID 12496842, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

64 gm (0.2 mol) of 4-(3-methyl-2-butenyl)-1,2-diphenyl-3,5-dioxo-pyrazolidine were dissolved in an aqueous sodium hydroxide solution obtained by dissolving 16 gm (0.4 mol) of sodium hydroxide pellets in 640 ml of water. The solution was heated for 7 hours. The reaction mixture was then cooled to room temperature and washed twice with ether. The ether extract contained a little hydrazobenzene. The aqueous alkaline solution was then made acid to Congo red with 10% hydrochloric acid and quickly extracted with ethyl ether. The organic phase was evaporated to dryness, leaving (3-methyl-2-butenyl)propanedioic acid mono(1,2-diphenyl hydrazide) as an oily residue which was dissolved in a dilute ammonium hydroxide solution obtained by diluting 40 ml of an aqueous 32% ammonium hydroxide solution with 600 ml of water. To this solution was added a solution of 11 gm of calcium chloride in 40 ml of water. The calcium salt of (3-methyl-2-butenyl)propanedioic acid mono(1,2-phenylhydrazide)dihydrate which precipitated upon stirring was suction filtered off and dried for 8 hours at 50° C. and 15 mmHg. The salt was obtained as a white solid. Yield: 54.06 gm (72% of theory), M.p. 166° C.

Workup

  1. customobtained
  2. temperatureThe solution was heated for 7 hours
  3. washwashed twice with ether
  4. extractionThe ether extract
  5. extractionquickly extracted with ethyl ether
  6. customThe organic phase was evaporated to dryness

Sources & evidence

ORD record
ord-e7cc8648d5ee4933986e7d4c24360c7b
Source dataset
uspto-grants-1981_11
Patent number
US04301177

Reaction notes

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