1,1'-Carbonyldiimidazole → 3,3,3-Trifluoro-2-hydroxy-2-methyl-N-[2-nitro-4-(phenylsulfonyl)phenyl]propanamide

HRID 374877Notes

Reaction equation

[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4](O)=[O:5].C(N1C=CN=C1)(N1C=CN=C1)=O.[N+:23]([C:26]1[CH:32]=[C:31]([S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)(=[O:35])=[O:34])[CH:30]=[CH:29][C:27]=1[NH2:28])([O-:25])=[O:24]>O1CCCC1>[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4]([NH:28][C:27]1[CH:29]=[CH:30][C:31]([S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)(=[O:35])=[O:34])=[CH:32][C:26]=1[N+:23]([O-:25])=[O:24])=[O:5]

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (1.00 g), 1,1'-carbonyldiimidazole (1.03 g) and dry tetrahydrofuran (25 mL) was heated, under N2, at 45° C. in an ultrasound bath for 0.5 hours. 2-Nitro-4-(phenylsulfonyl)aniline (1.75 g) was added, the mixture was heated at 45° C. for 18 hours; poured onto water (350 mL) and extracted with Et2O. The combined extracts were washed (brine), dried and evaporated to give an orange solid (3.01 g) that was purified by chromatographed, with chloroform as the eluent, to yield the title compound as a pale yellow solid (0.46 g); mp 191°-192.5° C.; MS: m/z=419(M+1); NMR: 1.58 (s,3), 7.63-7.76 (m,3), 8.02-8.07 (d,3), 8.34 (dd,1, J=2.2, 8.6), 8.59 (s,1), 8.61 (d,1, J=2.3). Analysis for C 16 H13F3N2O6S: Calculated: C, 45.94; H, 3.13; N, 6.70; Found: C, 45.95; H, 3.19; N, 6.53.

Workup

temperaturethe mixture was heated at 45° C. for 18 hours
additionpoured onto water (350 mL)
extractionextracted with Et2O
washThe combined extracts were washed (brine)
customdried
customevaporated

Sources & evidence

ORD record: ord-53a589256d1b440487859755c4909490
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05482969

Reaction notes

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