Water → 2-Chloro-4-phenylhydrazinoquinazoline

HRID 618653Notes

Reaction equation

HRID 618653 reaction equation
C(N(CC)C(C)C)(C)C.[C:10]1([NH:16][NH2:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O.[Cl:19][C:20]1[N:29]=[C:28](Cl)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1>C1COCC1>[Cl:19][C:20]1[N:29]=[C:28]([NH:17][NH:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7516PhenylhydrazineHCID 81531DiisopropylethylamineHCID 2528862,4-Dichloroquinazoline

Product 1

HCID 154288362-Chloro-4-phenylhydrazinoquinazoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N,N-diisopropylethylamine (10 ml, 57 mmol) in THF (150 ml), 2,4dichloroquinazoline [prepared according to the procedure described by Curd, F. H. S. et al., J. Chem. Soc., (1947), 775] (5 g, 25 mmol) and phenylhydrazine (2.7 g, 25 mmol) was added. After stirring for 30 minutes, the reaction was poured into water and extracted with dichloromethane (3×100 ml). The combined organic layers were dried over Na2SO4 and evaporated under reduced pressure. The resulting solid was triturated with ethanol and filtered to afford 2-chloro-4-phenylhydrazinoquinazoline (3.2 g ) as a yellow solid, m.p. 178° C. (dec.).

Workup

  1. extractionextracted with dichloromethane (3×100 ml)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customevaporated under reduced pressure
  4. customThe resulting solid was triturated with ethanol
  5. filtrationfiltered

Sources & evidence

ORD record
ord-be39c526ffab406fbd5763123b922d06
Source dataset
uspto-grants-1999_09
Patent number
US05955465

Reaction notes

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