Thionyl Chloride → HCID 12724786, compound

HRID 443856Notes

Reaction equation

HRID 443856 reaction equation
[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5](=[O:12])[N:4]2[N:13]=[C:14]([C:16]([NH2:18])=O)[CH:15]=[C:3]12.S(Cl)(Cl)=O>CN(C)C=O>[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5](=[O:12])[N:4]2[N:13]=[C:14]([C:16]#[N:18])[CH:15]=[C:3]12

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12724777HCID 12724777, compound

Product 1

HCID 12724786HCID 12724786, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
57 °C

Procedure

A mixture of 5.3 g of 4,9-dihydro-4-methyl-9-oxo-pyrazolo[5,1-b]quinazoline-2-carboxamide, 5.2 g of thionyl chloride and 65 ml of dimethylformamide is stirred and heated at 57° C. for 18 hrs, then evaporated at reduced pressure. The residue is stirred with 600 ml of water and the resulting solid 4,9-dihydro-4-methyl-9-oxo-pyrazolo[5,1-b]quinazoline-2-carbonitrile is collected by filtration, washed with water and dried; mp 307°-310° C., after crystallization from dimethylformamide/ethanol.

Workup

  1. customevaporated at reduced pressure
  2. stirringThe residue is stirred with 600 ml of water
  3. filtrationthe resulting solid 4,9-dihydro-4-methyl-9-oxo-pyrazolo[5,1-b]quinazoline-2-carbonitrile is collected by filtration
  4. washwashed with water
  5. customdried
  6. custommp 307°-310° C., after crystallization from dimethylformamide/ethanol

Sources & evidence

ORD record
ord-7ac2a6f0e8ce4a80b2321028d5399f13
Source dataset
uspto-grants-1981_04
Patent number
US04261997

Reaction notes

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