2-Fluoro-N-methyl-5-nitro-4-(2,2,2-trifluoroethoxy)benzenesulfonamide → HCID 67166735, compound

HRID 536059Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[C:5]([N+:14]([O-])=O)=[CH:4][C:3]=1[S:17]([NH:20][CH3:21])(=[O:19])=[O:18]>CO.[Pd]>[NH2:14][C:5]1[C:6]([O:8][CH2:9][C:10]([F:12])([F:13])[F:11])=[CH:7][C:2]([F:1])=[C:3]([S:17]([NH:20][CH3:21])(=[O:18])=[O:19])[CH:4]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of 2-fluoro-N-methyl-5-nitro-4-[(2,2,2-trifluoroethyl)oxy]benzene-sulfonamide (10 g, 30.1 mmol) in MeOH (150 mL) was treated with 10% Pd/C (1 g) and stirred under H2 (45 psi) at 45° C. for 10 hours before being filtered. The filtrate was concentrated to give 5-amino-2-fluoro-N-methyl-4-[(2,2,2-trifluoroethyl)oxy]benzene-sulfonamide (8 g, 88%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.40 (q, J=5.07 Hz, 1 H), 7.10 (d, J=11.69 Hz, 1 H), 7.05 (d, J=7.28 Hz, 1 H), 5.04 (s, 2 H), 4.83 (q, J=8.82 Hz, 2 H), 2.42 (d, J=4.41 Hz, 3 H). MS (m/z) 303.0 (M+H+).

Workup

filtrationbefore being filtered
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-a6d9f7d1cdc345cf818ba86698d30359
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859571B2

Reaction notes

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