Mefenamic acid → HCID 19815178, compound

HRID 465973Notes

Reaction equation

C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]2[C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]=1[CH3:30].Cl.[CH3:32][NH:33][OH:34]>CN(C=O)C>[CH3:30][C:15]1[C:14]([CH3:13])=[CH:19][CH:18]=[CH:17][C:16]=1[NH:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=1[C:27]([N:33]([OH:34])[CH3:32])=[O:28]

Participants

Conditions

Temperature: 24 °C

Procedure

1,1'-Carbonyl-diimidazole (5.35 g; 0.033 mol) is added to a solution of mefanamic acid (7.2% g; 0.03 mol) in dry DMF (100 ml). The solution is stirred at 24° C. for 20 hours and then briefly warmed to 50° C. N-Methylhydroxylamine hydrochloride (2.7 g; 0.032 mo) is added to the cooled solution at 24° C. and stirred for two days. The reaction mixture is then evaporated to dryness and the residue is taken up in CH2Cl2, washed with water, and dried over sodium sulfate and evaporated. The residue is flash chromatographed through silica gel and eluted with n-hexane-CH2Cl2 -EtOAc (2:1:1) yielding a crude product which is rechromatographed through silica gel and eluted with n-hexane-CH2Cl2 -EtOAc (4:5:1). The product is recrystallized from n-pentane to give white crystals. Yield 1.5 g (18.5%); mp 70°-71° C.

Workup

temperaturebriefly warmed to 50° C
stirringstirred for two days
customThe reaction mixture is then evaporated to dryness
washwashed with water
dry with materialdried over sodium sulfate
customevaporated
customchromatographed through silica gel
washeluted with n-hexane-CH2Cl2 -EtOAc (2:1:1)

Sources & evidence

ORD record: ord-c7932767935b474ea8f24eba2e61df76
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05155110

Reaction notes

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