Sodium Chloride → Cilostamide

HRID 1154937Notes

Reaction equation

HRID 1154937 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH:12]=[CH:11]2)([OH:3])=O.BrC(OC)=O.[CH3:24][NH:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[Na+].[Cl-]>O1CCCC1.N1C=CC=CC=1>[CH3:24][N:25]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13](=[O:18])[CH:12]=[CH:11]2)=[O:3]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 7514N-MethylcyclohexylamineHCID 128663424-((2-Oxo-1,2-dihydroquinolin-6-yl)oxy)butanoic acidHCID 15389422Methyl bromoformate

Product 1

HCID 2753Cilostamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.5 Grams of 6-(3-carboxy)propoxycarbostyril and 1.8 ml of pyridine are added to 50 ml of tetrahydrofuran, and then 1.0 ml of methyl bromoformate is added dropwise to said solution under external ice cooling and agitation while maintaining the internal temperature at 5°-15° C. after addition, the mixture is further agitated at room temperature for 1 hour and then added with 1.2 g of N-methylcyclohexylamine, followed by additional 3-hour agitation. The reaction solution is poured into 200 ml of saturated NaCl solution and the precipitated crystals are filtered out and washed with water. The obtained crude crystals are recrystallized from chloroform-ethanol to obtain 2.3 g of 6-[3-(N-methyl-N-cyclohexylaminocarbonyl)propoxy]carbostyril in the form of colorless needle-like crystals with m.p. of 184.5°-186° C.

Workup

  1. temperatureagitation while maintaining the internal temperature at 5°-15° C.
  2. additionafter addition
  3. waitfollowed by additional 3-hour
  4. filtrationthe precipitated crystals are filtered out
  5. washwashed with water
  6. customThe obtained crude crystals
  7. customare recrystallized from chloroform-ethanol

Sources & evidence

ORD record
ord-5810647647504145b573b3275219579e
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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