Sodium Chloride → HCID 15572903, compound

HRID 1154941Notes

Reaction equation

HRID 1154941 reaction equation
[C:1]([CH2:4][CH:5]([CH3:19])[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.C(=O)([O-])[O-].[K+].[K+].ClC(OCC(C)C)=O.[CH3:34][NH:35][CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH:37]1[CH3:42].[Na+].[Cl-]>CN(C)C=O>[CH3:34][N:35]([CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH:37]1[CH3:42])[C:1]([CH2:4][CH:5]([CH3:19])[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 5

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 62365Isobutyl chloroformateHCID 15921594HCID 15921594, compoundHCID 20563575HCID 20563575, compound

Product 1

HCID 15572903HCID 15572903, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.6 Grams of 6-(3-carboxy-2-methylpropoxy)-carbostyril and 1.4 g of potassium carbonate are added to 50 ml of dimethylformamide, followed by dropwise addition of 1.1 ml of isobutyl chloroformate under external ice cooling and agitation while maintaining the internal temperature at 10° to 20° C. After this dropwise addition, the mixture is agitated at 30° to 40° C. for 2 hours and then added with 1.6 ml of N-methyl-2-methylcyclohexylamine, followed by additional 2-hour agitation at the same temperature. 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 benzene-ligroin to obtain 0.9 g of 6-{3-[N-methyl-N-(2-methylcyclohexyl)-aminocarbonyl]-2-methylpropoxy}carbostyril in the form of colorless needle-like crystals. m.p., 146°-149° C.

Workup

  1. temperatureagitation while maintaining the internal temperature at 10° to 20° C
  2. additionAfter this dropwise addition
  3. waitfollowed by additional 2-hour
  4. filtrationthe precipitated crystals are filtered out
  5. washwashed with water
  6. customThe obtained crude crystals
  7. customare recrystallized from benzene-ligroin

Sources & evidence

ORD record
ord-7ab43ad42fc545de9a9000a7d4fb22ff
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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