Indomethacin → HCID 13654467, compound

HRID 542585Notes

Reaction equation

HRID 542585 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][C:38](=[CH2:40])[CH3:39])=[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][C:38](=[CH2:39])[CH3:40])=[O:35])=[O:24])=[C:2]2[CH3:1])=[O:12])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 3715IndomethacinHCID 11430Potassium CarbonateHCID 200405202-Methylprop-2-en-1-yl chloroacetate

Product 1

HCID 13654467HCID 13654467, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 180AcetoneSolvent

Procedure

10 g of indometacin, 4.0 g of potassium carbonate, 0.4 g of benzyltriethylammonium chloride and 60 ml of acetone are stirred for 30 minutes at 56° C. After addition of methallyl chloroacetate, stirring is continued for 3 hours at 40° C. (check by thin layer chromatography).

Sources & evidence

ORD record
ord-fbe28c54e3f24c5fa04ba40d04705088
Source dataset
uspto-grants-1987_04
Patent number
US04658039

Reaction notes

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