Thionyl Chloride → HCID 12724787, compound

HRID 443857Notes

Reaction equation

HRID 443857 reaction equation
[Cl: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>[Cl: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 12724778HCID 12724778, compound

Product 1

HCID 12724787HCID 12724787, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
56 °C

Procedure

A mixture of 3.0 g of 7-chloro-4,9-dihydro-4-methyl-9-oxo-pyrazolo[5,1-b]quinazoline-2-carboxamide, 1.6 ml of thionyl chloride and 35 ml of dimethylformamide is stirred and heated at 56° C. for 18 hrs, then evaporated at reduced pressure. The residue is stirred with 600 ml of water for 1 hour and the resulting solid 7-chloro-4,9-dihydro-4-methyl-9-oxo-pyrazolo[5,1-b]-quinazoline-2-carbonitrile is collected by filtration, washed with water and dried; mp 350° C., after crystallization from dimethylformamide/ethanol.

Workup

  1. customevaporated at reduced pressure
  2. stirringThe residue is stirred with 600 ml of water for 1 hour
  3. filtrationthe resulting solid 7-chloro-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 350° C., after crystallization from dimethylformamide/ethanol

Sources & evidence

ORD record
ord-39e18c1ffeda4b68bd11abb7f187c5aa
Source dataset
uspto-grants-1981_04
Patent number
US04261997

Reaction notes

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