Hydrochloric Acid → HCID 18962905, compound

HRID 1194708Notes

Reaction equation

HRID 1194708 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[O:14][CH2:15][C:10]=3[C:9]([C:20](=[O:24])[CH2:21][C:22]#[N:23])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:25]1([N:31]=[C:32]=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C.Cl>CN(C)C=O>[C:22]([CH:21]([C:20]([C:9]1[C:10]2[CH2:15][O:14][C:13]3[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=3[C:11]=2[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=1)=[O:24])[C:32]([NH:31][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:33])#[N:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 21268432HCID 21268432, compound

Product 1

HCID 18962905HCID 18962905, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(1,4-dihydro-1-phenyl-[1]-benzopyrano[4,3-c]pyrazol-3-yl)-3-oxo-propanenitrile (2.1 g) is reacted with phenyl isocyanate (0.8 g) in the presence of triethylamine (0.75 g) in dimethylformamide (20 ml) under stirring at 25°-30° C. for 90 minutes. The reaction mixture is diluted with ice water, acidified to pH 2 with HCl and the precipitate is filtered and washed with water. Crystallization from dichloromethane/methanol gives 2.5 g of 2-cyano-3-(1,4-dihydro-1-phenyl-[1]-benzopyrano[4,3-c]pyrazol-3-yl)-3-oxo-N-phenyl-propanamide, m.p. 280°-282° C., NMR (CDCl3) δppm: 5.54 (s) (2H, --CH2O--), 6.7-7.7 (m) (14H, phenyl protons), 8.94 (s) (1H, CONH--), 16.4 (bs) (1H, enol).

Workup

  1. filtrationthe precipitate is filtered
  2. washwashed with water
  3. customCrystallization from dichloromethane/methanol

Sources & evidence

ORD record
ord-2eb6cf00c2e2433db3b0272e454a5ac0
Source dataset
uspto-grants-1989_03
Patent number
US04816467

Reaction notes

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