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

HRID 1292075Notes

Reaction equation

HRID 1292075 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 The reaction mixture
  2. temperaturewas then cooled
  3. customwhite solid was separated which
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-a30d5cde3f5b46dda8c30c68ac198642
Source dataset
uspto-grants-1998_05
Patent number
US05756502

Reaction notes

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