Methacrolein → Apricoxib

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([S:20](=[O:23])(=[O:22])[NH2:21])=[CH:16][CH:15]=2)[C:11]#N)=[CH:6][CH:5]=1)[CH3:2].O=[CH:25][C:26](=C)[CH3:27]>>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([S:20](=[O:23])(=[O:22])[NH2:21])=[CH:16][CH:15]=3)[CH:25]=[C:26]([CH3:27])[CH:11]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

Reactant 2

HCID 6562Methacrolein

HCID 21862743HCID 21862743, compound

Product 1

HCID 9820073Apricoxib

Procedure

Following a procedure similar to that described in Example 1(iii), but using α-(4-ethoxyphenyl)-α-(4-sulfamoylanilino)acetonitrile [prepared as described in step (ii) above] and methacrolein as starting materials, the title compound was obtained as a brown powder (yield 3%), melting at 135-139° C.

Sources & evidence

ORD record: ord-7e50f84397864ba782b1db7198030486
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05908858

Reaction notes

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