Diethyl isopropylidenemalonate → N-(4-fluorophenyl)-N-isopropyl-2-(1-methylethylidene)-N'-((E)-styrylsulfonyl)malonamide

HRID 1256921Notes

Reaction equation

[CH3:1][C:2](=[C:4]([C:10]([O:12]CC)=O)[C:5]([O:7]CC)=O)[CH3:3].[CH:15](/[S:23]([NH2:26])(=[O:25])=[O:24])=[CH:16]\[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[F:27][C:28]1[CH:37]=[CH:36][C:31]([NH:32][CH:33]([CH3:35])[CH3:34])=[CH:30][CH:29]=1>>[F:27][C:28]1[CH:37]=[CH:36][C:31]([N:32]([CH:33]([CH3:35])[CH3:34])[C:10](=[O:12])[C:4](=[C:2]([CH3:1])[CH3:3])[C:5]([NH:26][S:23](/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:24])=[O:25])=[O:7])=[CH:30][CH:29]=1

Participants

Reactant 3

HCID 81255Diethyl isopropylidenemalonate

HCID 154403Benzenamine, 4-fluoro-N-(1-methylethyl)-

HCID 5357731(1E)-2-Phenylethenesulfonamide

Product 1

HCID 68511856N-(4-fluorophenyl)-N-isopropyl-2-(1-methylethylidene)-N'-((E)-styrylsulfonyl)malonamideYield 0.6%

Procedure

Diethyl (1-methylethylidene)malonate (5.00 g) was subjected to hydrolysis in the same manner as in Example 1 (1). The obtained carboxylic acid and trans-β-styrenesulfonamide (953 mg) were condensed in the same manner as in Example 152 (3), and the condensed product was subjected to hydrolysis in the same manner as in Example 1 (3). This and 4-fluoro-N-isopropylaniline (805 mg) were condensed in the same manner as in Example 1 (4) to give a crude product. This was purified by silica gel column chromatography to give the title compound (13 mg) as a white powder.

Workup

customto give a crude product
customThis was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-2a7f4ed45600435382159c2fc741a5e5
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461209B2

Reaction notes

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