Dimethylformamide → HCID 14178554, compound

HRID 477903Notes

Reaction equation

HRID 477903 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH3:19])=[C:9]1[S:20]([C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21].[C:30](=O)([O-])[O-].[K+].[K+].CI.CN(C)C=O>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH3:19])=[C:9]1[S:20]([C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14722815HCID 14722815, compound

Product 1

HCID 14178554HCID 14178554, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(2-chlorophenyl)-3-(4-hydroxyphenyl)sulfonyl-5-methoxycarbonyl-2,6-dimethyl-1,4-dihydropyridine (4.33 g), potassium carbonate (2.76 g), methyl iodide (5.68 g), and N,N-dimethylformamide (DMF) (25 ml) was stirred at room temperature for 24 hours. The reaction mixture was diluted with water (250 ml) and extracted with ethyl acetate. The extract was dried over magnesium sulfate, filtered, and evaporated to dryness. The residue was crystallized from ether to give 4-(2-chlorophenyl)-3-(4-methoxyphenyl)sulfonyl-5-methoxycarbonyl-2,6-dimethyl-1,4-dihydropyridine, m.p. 176°-178°.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-2aaa8df77f784f59ab8baf94b6e1eb92
Source dataset
uspto-grants-1989_12
Patent number
US04889866

Reaction notes

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