Hydrazine → 2-Hydrazino-3-(3-isopropoxy-phenyl)-3H-quinazolin-4-one

HRID 362601Notes

Reaction equation

HRID 362601 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=S)[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].[NH2:23][NH2:24]>C(O)C>[NH:23]([C:12]1[N:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH:6]=2)[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1)[NH2:24]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 108289213-(3-Isopropoxy-phenyl)-2-thioxo-2,3-dihydro-1H-quinazolin-4-one

Product 1

HCID 106148972-Hydrazino-3-(3-isopropoxy-phenyl)-3H-quinazolin-4-oneYield 38.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(3-isopropoxy-phenyl)-2-thioxo-2,3-dihydro-1H-quinazolin-4-one (Example 1) (3.12 g, 10 mmol) and anhydrous hydrazine (3.2 g, 100 mmol) in 100 mL of ethanol was refluxed for 18 hours. The reaction mixture was then cooled and white solid was separated which was filtered to obtain 1.2 g (38%) of title compound as white solid. The filtrate was concentrated and an additional 1.6 g (50.4%) of title compound was isolated by crystallization from ethyl acetate, mp 158°-160° C.

Workup

  1. temperaturewas refluxed for 18 hours
  2. temperatureThe reaction mixture was then cooled
  3. customwhite solid was separated which
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-1f98c093de0e4785ad3cd43a8af2b8ea
Source dataset
uspto-grants-1999_02
Patent number
US05869665

Reaction notes

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