Hydrazine hydrate (1:1) → Prizidilol

HRID 1763302Notes

Reaction equation

HRID 1763302 reaction equation
[C:1]([NH:5][CH2:6][CH:7]([OH:23])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:17]=[CH:18][C:19](=S)[NH:20][N:21]=1)([CH3:4])([CH3:3])[CH3:2].O.[NH2:25][NH2:26]>>[C:1]([NH:5][CH2:6][CH:7]([OH:23])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:21]=[N:20][C:19]([NH:25][NH2:26])=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13530383HCID 13530383, compound

Product 1

HCID 71952Prizidilol

Procedure

A stirred mixture of 6-[2-(3-t-butylamino-2-hydroxypropoxy)phenyl]-3(2H)-pyridazinethione (2 g, 0.006 mole) and hydrazine hydrate (50 ml) was heated under reflux in an atmosphere of nitrogen for 90 minutes. Excess of hydrazine hydrate was removed under reduced pressure and 3-[2-(3-t-butylamino-2-hydroxypropoxy)phenyl]-6-hydrazinopyridazine was isolated as the hemisulphate hemihydrate (2.34 g, 98%, m.p. 180°-185° ). Recrystallisation from aqueous ethanol gave a crystalline material of m.p. 200°-203° (decomposition). (Found: C, 52.41; H, 6.76; N, 17.78; M+, 331. C17H25N5O2. 1/2H2SO4. 1/2H2O requires: C, 52.43; H, 6.99; N, 17.98%; M(base), 331).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in an atmosphere of nitrogen for 90 minutes
  3. customExcess of hydrazine hydrate was removed under reduced pressure

Sources & evidence

ORD record
ord-5f9a44f435e8473dbbf58f8586a02b3a
Source dataset
uspto-grants-1978_09
Patent number
US04111936

Reaction notes

Loading…