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

HRID 1075384Notes

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 C16H13F3N2O6S: 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-f353334caf4f4a45930bf5412dbde376
Source dataset: uspto-grants-1999_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05900432

Reaction notes

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