Hydrochloric Acid → HCID 21249378, compound

HRID 1194711Notes

Reaction equation

HRID 1194711 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[H-].[Na+].[C:9]1([N:15]2[C:19]3[C:20]4[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=4[S:22][CH2:23][C:18]=3[C:17]([C:28](Cl)=[O:29])=[N:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>CN(C)C=O.O1CCOCC1>[C:1]([CH:3]([C:28]([C:17]1[C:18]2[CH2:23][S:22][C:21]3[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=3[C:19]=2[N:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:16]=1)=[O:29])[C:4]([NH2:6])=[O:5])#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7898CyanoacetamideHCID 24758Sodium hydrideHCID 19808360HCID 19808360, compound

Product 1

HCID 21249378HCID 21249378, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Cyanoacetamide (1.85 g) is treated with 50% sodium hydride (1.28 g) in dimethylformamide (35 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 (6.53 g), prepared according to Example 15, dissolved in dioxane (35 ml) is added under stirring at room temperature. The reaction mixture is allowed to react for 2 hours, then is diluted with ice water and acidified to pH 1 with 37% HCl. The gummy precipitate is extracted with ethyl acetate and the organic solution washed with N HCl and then evaporated to dryness in vacuo. The residue is purified over SiO2 column, using chloroform/methanol 80:20 as eluent, to give 2-cyano-3-(1,4-dihydro-1-phenyl-[1]-benzothiopyrano[4,3-c]pyrazol-3-yl)-3-oxo-propanamide, m.p. >300° C. dec., NMR (DMSO d6) δ ppm: 4.10 (s) (2H, --S--CH2 --), 6.00-7.00 (bs) (2H, CONH2), 6.60-7.80 (m) (9H, phenyl protons), 9.00 (bs) (1H, OH).

Workup

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

Sources & evidence

ORD record
ord-fa29461c5ad54385b490d97f4737224d
Source dataset
uspto-grants-1989_03
Patent number
US04816467

Reaction notes

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