Thionyl Chloride → HCID 12724788, compound

HRID 443858Notes

Reaction equation

HRID 443858 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7]3=[CH:13][C:14]([C:16]([NH2:18])=O)=[N:15][N:6]3[C:5](=[O:19])[C:4]=2[CH:3]=1.S(Cl)(Cl)=O>CN(C)C=O>[F:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7]3=[CH:13][C:14]([C:16]#[N:18])=[N:15][N:6]3[C:5](=[O:19])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12724779HCID 12724779, compound

Product 1

HCID 12724788HCID 12724788, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 9.2 g of 7-fluoro-4,9-dihydro-4-methyl-9-oxo-pyrazolo[5,1-b]quinazoline-2-carboxamide, 25 ml of thionyl chloride and 175 ml of dimethylformamide is stirred and heated at 65° C. for 20 hours, then evaporated at reduced pressure. The residue is stirred with 1 liter of ice water and the resulting solid 7-fluoro-4,9-dihydro-4-methyl-9-oxo-pyrazolo[5,1-b]-quinazoline-2-carbonitrile is collected by filtration, washed with water and dried; mp 331°-340° C., after crystallization from dimethylformamide/ethanol.

Workup

  1. customevaporated at reduced pressure
  2. stirringThe residue is stirred with 1 liter of ice water
  3. filtrationthe resulting solid 7-fluoro-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 331°-340° C., after crystallization from dimethylformamide/ethanol

Sources & evidence

ORD record
ord-f34973f1291240539985d333e574cbde
Source dataset
uspto-grants-1981_04
Patent number
US04261997

Reaction notes

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