Water → 4-(Hydroxymethyl)-4-methyl-1-phenylpyrazolidin-3-one

HRID 1762978Notes

Reaction equation

HRID 1762978 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9](=[O:12])(O)[O-].[Na+].[C:14]1([CH3:20])[CH:19]=CC=C[CH:15]=1.[OH2:21]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[OH:21][CH2:15][C:14]1([CH3:20])[CH2:19][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:8][C:9]1=[O:12]

Participants

6

Reactant 4

HCID 962Water2×HCID 1140TolueneHCID 7516PhenylhydrazineHCID 516892Sodium Bicarbonate

Product 1

HCID 922384-(Hydroxymethyl)-4-methyl-1-phenylpyrazolidin-3-one

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 0.163 kg (1.5 mol) phenylhydrazine, 0.630 kg (7.5 mol) sodium bicarbonate, 0.75 L toluene, 75 mL of water and 3.0 g (0.013 mol) benzyl triethylammonium chloride heated to and maintained at 60° to 70° C. while 0.466 kg (ca 2.05 mol) of 1-methyl-4-oxo-3,5-dioxa-4-thiocyclohexane carbonyl chloride are added over a period of four hours. The reaction mixture is held at 70° C. for 1 hour, and 1.5 L of water added. The reaction mixture is then heated to 80° C. and held for one additional hour at this temperature before the lower aqueous phase is decanted. Residual water is then removed by azeotropic distillation, 0.120 L of isopropanol are added at 70° C., and crystallization is induced by cooling to 0° to 5° C. The product is isolated by filtration, washed with two 0.1 L 0° to 5° C. toluene washes, and dried in a 70° C. forced-air oven overnight. Approximately 0.229 kg (1.11 mol, 74% of theoretical amount) of 4-hydroxymethyl-4-methyl-1-phenyl-3-pyrozolidinone is isolated. The IR and NMR(H) spectra match those of this compound, M.P.: 121.8° to 123.3° C.

Workup

  1. temperatureheated to and
  2. additionare added over a period of four hours
  3. customis decanted
  4. customResidual water is then removed by azeotropic distillation, 0.120 L of isopropanol
  5. additionare added at 70° C.
  6. customcrystallization
  7. temperatureby cooling to 0° to 5° C
  8. customThe product is isolated by filtration
  9. washwashed with two 0.1 L 0° to 5° C. toluene washes
  10. customdried in a 70° C. forced-air oven overnight
  11. customApproximately 0.229 kg (1.11 mol, 74% of theoretical amount) of 4-hydroxymethyl-4-methyl-1-phenyl-3-pyrozolidinone is isolated

Sources & evidence

ORD record
ord-24798e06ef774f2295028511f6f9a8ef
Source dataset
uspto-grants-1989_05
Patent number
US04835285

Reaction notes

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