Propyl mercaptan → 2-Nitro-5-propylsulfanyl-4-trifluoromethyl-phenylamine

HRID 408723Notes

Reaction equation

Cl[C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22]([SH:25])[CH2:23][CH3:24]>CN(C=O)C>[N+:9]([C:5]1[CH:4]=[C:3]([C:12]([F:15])([F:14])[F:13])[C:2]([S:25][CH2:22][CH2:23][CH3:24])=[CH:7][C:6]=1[NH2:8])([O-:11])=[O:10]

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 5-chloro-2-nitro-4-trifluoromethyl-phenylamine (1.50 g, 6.26 mmol), potassium carbonate (1.72 g, 12.5 mmol), and DMF (31 mL) was added 1-propanethiol (0.620 mL, 6.86 mmol). The reaction mixture was heated at 90° C. for 16 h, then allowed to cool to 23° C. and poured into ice/brine (300 mL). The resulting yellow precipitate was collected to yield the titled compound (1.67 g, 95%). MS (ESI/CI): mass calcd. for C10H11F3N2O2S, 280.1; m/z found, 281.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.41 (s, 1H), 6.58 (s, 1H), 6.36 (br s, 2H), 2.97 (t, J=7.3 Hz, 2H), 1.87-1.72 (m, 2H), 1.10 (t, J=7.4 Hz, 3H).

Workup

temperatureto cool to 23° C.
customThe resulting yellow precipitate was collected

Sources & evidence

ORD record: ord-c83b1738b5584adf9d998a6ad73d5edf
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759345B2

Reaction notes

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