Hydrochloric Acid → HCID 86742836, compound

HRID 1194705Notes

Reaction equation

HRID 1194705 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[H-].[Na+].[C:11]1([N:17]2[C:21]3[C:22]4[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=4[S:24][CH2:25][C:20]=3[C:19]([C:30](Cl)=[O:31])=[N:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>CN(C)C=O>[C:1]([CH:3]([C:30]([C:19]1[C:20]2[CH2:25][S:24][C:23]3[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=3[C:21]=2[N:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:18]=1)=[O:31])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 19808360HCID 19808360, compound

Product 1

HCID 86742836HCID 86742836, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Ethyl cyanoacetate (1.4 g) is treated with 50% sodium hydride (0.58 g) in dimethylformamide (10 ml) under stirring at room temperature until the effervescence subsides. To this solution 1,4-dihydro-1-phenyl-[1]-benzothiopyrano[4,3-c]pyrazole-3-carbonyl chloride (3.26 g), prepared according to Example 5, dissolved in dimethylformamide (10 ml) is added under stirring at room temperature. The reaction mixture is allowed to react for 20 hours, then it is diluted with ice water and acidified to pH 3 with 37% HCl. The precipitate is extracted with ethyl acetate and the organic solution washed with water and then evaporated to dryness in vacuo. The residue is purified over a SiO2 column, using hexane-ethyl acetate 80:20 as eluent, to give 2-cyano-3-(1,4-dihydro-1-phenyl-[1]-benzothiopyrano[4,3-c]pyrazol-3-yl)-3-oxo-propanoic acid, ethyl ester (2.4 g), m.p. 176°-178° C., which is reacted with aniline (1.7 g) in xylene (100 ml) at the reflux temperature for 48 hours. After cooling the precipitate is filtered and washed with xylene, then crystallized from dichloromethane/methanol to give 1.5 g of 2 -cyano-3-(1,4-dihydro-1-phenyl-[1]-benzothiopyrano[4,3-c]pyrazol-3-yl)-3-oxo-N-phenyl-propanamide, m.p. 228°-230° C.

Workup

  1. additionis added
  2. stirringunder stirring at room temperature
  3. customto react for 20 hours
  4. extractionThe precipitate is extracted with ethyl acetate
  5. washthe organic solution washed with water
  6. customevaporated to dryness in vacuo
  7. customThe residue is purified over a SiO2 column

Sources & evidence

ORD record
ord-8a648fe4f3a64c5aa66bc4ab02038b20
Source dataset
uspto-grants-1989_03
Patent number
US04816467

Reaction notes

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