Sodium Chloride → Cilostamide

HRID 1154953Notes

Reaction equation

HRID 1154953 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.C([O-])([O-])=O.[K+].[K+].[I-].[Na+].[CH3:21][N:22]([CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C:23](=[O:28])[CH2:24][CH2:25][CH2:26]Cl.[Na+].[Cl-]>CN(C=O)C>[CH3:21][N:22]([CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C:23]([CH2:24][CH2:25][CH2:26][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2)=[O:28]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1770652,6-DihydroxyquinolineHCID 132082974-Chloro-N-cyclohexyl-N-methylbutanamide

Product 1

HCID 2753Cilostamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.6 Grams of 6-hydroxycarbostyril, 1.4 g of K2CO3, 1.6 g of sodium iodide and 2.5 g of N-methyl-N-(4-chlorobutyryl)cyclohexylamine are added to 30 ml of DMF and the mixture is agitated at 70° to 80° C. for 4 hours. After the reaction, the reaction solution is poured into 200 ml of saturated NaCl solution and the precipitated crystals are filtered out and washed with water. The resultant crude crystals are recrystallized from chloroformethanol to obtain 1.5 g of 6-[3-(N-methyl-N-cyclohexylaminocarbonyl)propoxy]carbostyril in the form of colorless needle-like crystals with melting point of 184.5°-186° C.

Workup

  1. customAfter the reaction
  2. filtrationthe precipitated crystals are filtered out
  3. washwashed with water
  4. customThe resultant crude crystals are recrystallized from chloroformethanol

Sources & evidence

ORD record
ord-d81d36cf128a44aa9cb243a2f1979625
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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