Mefenamic acid → HCID 7968207, compound

HRID 1461122Notes

Reaction equation

HRID 1461122 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[C:16]([OH:18])=[O:17])[C:7]=1[CH3:8].Cl[CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22].C(N(CC)CC)C.[I-].[Na+]>CN(C)C=O.O>[CH3:8][C:7]1[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=1[NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=1[C:16]([O:18][CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])=[O:17]

Participants

7

Reactant 4

HCID 4044Mefenamic acidHCID 5238Sodium IodideHCID 8471TriethylamineHCID 758862-chloro-N,N-dimethylacetamide

Product 1

HCID 7968207HCID 7968207, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of mefenamic acid (2.41 g, 0.01 mole), 2-chloro-N,N-dimethylacetamide (1.6 g, 0.013 mole), triethylamine (1.6 ml, 0.011 mole) and sodium iodide (0.15 g, 0.001 mole) in N,N-dimethylformamide (10 ml) was stirred at 90° C. for 2 h. Water (50 ml) was added and the mixture allowed to stand at 4° C. for 5 h. The title compound was isolated by filtration, washed with water and recrystallized from ethanol-water (3.0 g, 92%). Mp 85°-86° C.

Workup

  1. waitto stand at 4° C. for 5 h

Sources & evidence

ORD record
ord-053b2e4becfd46b68c87891ccbabeba2
Source dataset
uspto-grants-1991_12
Patent number
US05073641

Reaction notes

Loading…