Thionyl Chloride → HCID 19808360, compound

HRID 373851Notes

Reaction equation

HRID 373851 reaction equation
[C:1]1([N:7]2[C:11]3[C:12]4[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=4[S:14][CH2:15][C:10]=3[C:9]([C:20]([OH:22])=O)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:25])=O>O1CCOCC1>[C:1]1([N:7]2[C:11]3[C:12]4[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=4[S:14][CH2:15][C:10]=3[C:9]([C:20]([Cl:25])=[O:22])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 3309831-Phenyl-1,4-dihydrothiochromeno(4,3-c)pyrazole-3-carboxylic acid

Product 1

HCID 19808360HCID 19808360, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,4-Dihydro-1-phenyl-[1]-benzothiopyrano[4,3-c]pyrazole-3-carboxylic acid (2 g) is reacted with thionyl chloride (1 ml) in dioxane (40 ml) at reflux temperature for 2 hours. After cooling the solution is evaporated to dryness in vacuo to give 1,4-dihydro-1-phenyl-[1]-benzothiopyrano[4,3-c]pyrazole-3-carbonyl chloride as crystalline residue. The crude product is dissolved in anhydrous dioxane (15 ml) and reacted for 2 h under stirring at room temperature with the carbanion obtained by treatment of cyanacetic acid, 2-morpholinomethylbenzylamide (1.95 g) with 50% sodium hydride (0.39 g) in anhydrous dioxane/dimethylformamide 9:1 (20 ml) at room temperature.

Workup

  1. temperatureat reflux temperature for 2 hours
  2. temperatureAfter cooling the solution
  3. customis evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-3df0fad69f57488bb8d65ecebfca6bc7
Source dataset
uspto-grants-1992_11
Patent number
US05166152

Reaction notes

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