Hydrazine hydrate (1:1) → Prizidilol

HRID 972764Notes

Reaction equation

HRID 972764 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 an oil which was characterised 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).

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-0552a0ed4b1e431bb0bb6e01a9da67ff
Source dataset
uspto-grants-1977_10
Patent number
US04053601

Reaction notes

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