Indomethacin → HCID 70430505, compound

HRID 542584Notes

Reaction equation

HRID 542584 reaction equation
[CH3:1][C:2]1[N:10]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:20][CH3:21])=[CH:5][C:4]=2[C:3]=1[CH2:22][C:23]([OH:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:33][C:34]([O:36][CH2:37][CH:38]=[CH:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:35]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CC(C)=O>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]([N:10]2[C:9]3[C:4](=[CH:5][C:6]([O:20][CH3:21])=[CH:7][CH:8]=3)[C:3]([CH2:22][C:23]([O:25][CH2:33][C:34]([O:36][CH2:37][CH:38]=[CH:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[O:35])=[O:24])=[C:2]2[CH3:1])=[O:12])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 3715IndomethacinHCID 11430Potassium CarbonateHCID 575458HCID 575458, compound

Product 1

HCID 70430505HCID 70430505, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 180AcetoneSolvent

Procedure

10 g of indometacin, 4 g of potassium carbonate, 0.3 g of benzyltriethylammonium chloride and 50 ml of acetone are stirred for 30 minutes at 50°-60° C. After addition of 6.32 g of cinnamyl chloroacetate stirring is continued for 3 to 4 hours at 40° C. (check by thin layer chromatography). After filtration, and distilling off the solvent, the residue is recrystallized first from ether/petroleum ether and then from acetone/water.

Workup

  1. filtrationAfter filtration
  2. distillationdistilling off the solvent
  3. customthe residue is recrystallized first from ether/petroleum ether

Sources & evidence

ORD record
ord-c59fad459cd348eb81f884d30f328c8e
Source dataset
uspto-grants-1987_04
Patent number
US04658039

Reaction notes

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