Methyl iodide → HCID 19808338, compound

HRID 373854Notes

Reaction equation

HRID 373854 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:16][CH2:15][C:14]3[C:13]([C:17](=[O:30])[CH:18]([C:28]#[N:29])[C:19]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:20])=[N:12][N:11]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:10]=3[C:8]=2[CH:9]=1)([OH:3])=[O:2].CI.[C:39](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:28]([CH:18]([C:17]([C:13]1[C:14]2[CH2:15][S:16][C:7]3[CH:6]=[CH:5][C:4]([C:1]([O:3][CH3:39])=[O:2])=[CH:9][C:8]=3[C:10]=2[N:11]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:12]=1)=[O:30])[C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20])#[N:29]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 19808321HCID 19808321, compound

Product 1

HCID 19808338HCID 19808338, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(8-Carboxy-1,4-dihydro-1-phenyl-[1]-benzothiopyrano[4,3-c]pyrazol-3-yl)-2-cyano-3-oxo-N-phenyl-propanamide (0.65 g) dissolved in dimethylformamide (50 ml) is reacted with methyl iodide (0.37 g) in the presence of anhydrous potassium carbonate (0.36 g) under stirring at room temperature for 2 hours. The reaction mixture is diluted with ice water and the precipitate is filtered, dissolved in chloroform and washed with 1N HCl and then with water. Evaporation of the solvent in vacuo gives a residue which is crystallized from CH2Cl2 /methanol to yield 0.48 g of 2-cyano-3-(1,4-dihydro-8-methoxycarbonyl-1-phenyl-[1]-benzothiopyrano[4,3-c]pyrazol-3-yl)-3-oxo-N-phenyl-propanamide, m.p. 228°-230° C.

Workup

  1. filtrationthe precipitate is filtered
  2. dissolutiondissolved in chloroform
  3. washwashed with 1N HCl
  4. customEvaporation of the solvent in vacuo
  5. customgives a residue which
  6. customis crystallized from CH2Cl2 /methanol

Sources & evidence

ORD record
ord-60db59c1c9de437aa9dd4ee65e170e92
Source dataset
uspto-grants-1992_11
Patent number
US05166152

Reaction notes

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