1,1'-Carbonyldiimidazole → N-[4-(N,N-Diethylaminosulfonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide

HRID 1938171Notes

Reaction equation

[F:1][C:2]([F:10])([F:9])[C:3]([CH3:8])([OH:7])[C:4](O)=[O:5].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:23]([N:25]([CH2:36][CH3:37])[S:26]([C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH3:24]>O1CCCC1>[CH2:36]([N:25]([CH2:23][CH3:24])[S:26]([C:29]1[CH:35]=[CH:34][C:32]([NH:33][C:4](=[O:5])[C:3]([OH:7])([CH3:8])[C:2]([F:10])([F:9])[F:1])=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH3:37]

Participants

Conditions

Temperature: 22 °C

Procedure

To a solution of α-trifluoromethyl lactic acid (0.37 g) in dry tetrahydrofuran (10 ml) at 22° C. was added carbonyldiimidazole (0.38 g) in one portion. The mixture was stirred for 30 minutes, then treated with 4-(N,N-diethylaminosulfonyl)aniline (0.53 g) and stirred at 22° C. for 1 hour followed by heating at reflux for 18 hours. After cooling to 22° C., the mixture was concentrated to an oil which was purified by chromatography (9:1 CH2Cl2 : diethyl ether) and crystallization from hexane to produce the title compound as a colourless crystalline solid (0.15 g); mp 115°-130° C.; MS: m/z=341(M+1); NMR (250 MHz, CDCl3): 1.12 (t,6), 1.78 (s,3), 3.22 (s,4), 3.73 (s,1), 7.67-7.79 (m,4), 8.62(broad s,1). Analysis for C14H19F3N2O4S: Calculated: C, 45.64; H, 5.19; N, 7.61; Found: C, 45.74; H, 5.22; N, 7.66.

Workup

stirringstirred at 22° C. for 1 hour
temperatureby heating
temperatureat reflux for 18 hours
concentrationthe mixture was concentrated to an oil which
customwas purified by chromatography (9:1 CH2Cl2 : diethyl ether) and crystallization from hexane

Sources & evidence

ORD record: ord-f38f776b6c1140028a5b6ad68ec76df8
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05693639

Reaction notes

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