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

HRID 1521394Notes

Reaction equation

HRID 1521394 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-84b9f9bdb92c4ff7943d0bdfa5c0b895
Source dataset
uspto-grants-2015_07
Patent number
US09073923B2

Reaction notes

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