Thionyl Chloride → HCID 12724789, compound

HRID 443859Notes

Reaction equation

HRID 443859 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[N:13]([CH3:17])[C:12]3=[CH:18][C:19]([C:21]([NH2:23])=O)=[N:20][N:11]3[C:10](=[O:24])[C:9]=2[CH:8]=1>CN(C)C=O>[CH3:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[N:13]([CH3:17])[C:12]3=[CH:18][C:19]([C:21]#[N:23])=[N:20][N:11]3[C:10](=[O:24])[C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12724780HCID 12724780, compound

Product 1

HCID 12724789HCID 12724789, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Thionyl chloride (1.5 ml) is added slowly, with stirring to 50 ml of dimethylformamide at 0° C. To this solution is added 2.9 g of 4,9-dihydro-7-methoxy-4-methyl-9-oxo-pyrazolo[5,1-b]quinazoline-2-carboxamide and the mixture is stirred and heated at 50° C. for 18 hrs, then evaporated at reduced pressure. The residue is stirred with 600 ml of ice water and the resulting solid 4,9-dihydro-7-methoxy-4-methyl-9-oxo-pyrazolo-[5,1-b]quinazoline-2-carbonitrile is collected by filtration, washed with water and dried; mp 316°-320° C. after crystallization from dimethylformamide/ethanol.

Workup

  1. customevaporated at reduced pressure
  2. stirringThe residue is stirred with 600 ml of ice water
  3. filtrationthe resulting solid 4,9-dihydro-7-methoxy-4-methyl-9-oxo-pyrazolo-[5,1-b]quinazoline-2-carbonitrile is collected by filtration
  4. washwashed with water
  5. customdried
  6. custommp 316°-320° C. after crystallization from dimethylformamide/ethanol

Sources & evidence

ORD record
ord-a82a8c4596924a1db6478a8c79124422
Source dataset
uspto-grants-1981_04
Patent number
US04261997

Reaction notes

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