Water → 5-Methylsulfanyl-2-nitro-4-trifluoromethyl-phenylamine

HRID 538154Notes

Reaction equation

HRID 538154 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.CN(C=O)C.[CH3:21][S-:22].[Na+].O>[Cl-].[Na+].O>[CH3:21][S:22][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

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 27738135-Chloro-2-nitro-4-(trifluoromethyl)anilineHCID 4378561Sodium methanethiolate

Product 1

HCID 669372705-Methylsulfanyl-2-nitro-4-trifluoromethyl-phenylamineYield 95.3%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-chloro-2-nitro-4-trifluoromethyl-phenylamine (2.02 g, 8.40 mmol) and DMF (40 mL) was added sodium thiomethoxide (0.618 g, 8.82 mmol). The mixture was heated to 90° C. for 50 min, then poured into brine. Water was added to bring the total volume to 300 mL and the orange precipitate was collected to yield the titled compound (2.02 g, 95%). 1H NMR (400 MHz, CDCl3): 8.42 (s, 1H), 6.51 (s, 1H), 6.39 (br s, 2H), 2.53 (s, 3H).

Workup

  1. customthe orange precipitate was collected

Sources & evidence

ORD record
ord-1ebe0d9271544963867f8cf1c6ebf44e
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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