Ethanol → 2-Chloro-3-fluoro-4-[4-(N-methyl-N-ethylcarbamoyl)phenylsulphanyl]aniline

HRID 2120378Notes

Reaction equation

HRID 2120378 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([S:9][C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:21])[N:17]([CH3:20])[CH2:18][CH3:19])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[N+:22]([O-])=O.CCO.O.C(=O)(O)[O-].[Na+]>Cl.[Fe].CCOC(C)=O>[Cl:1][C:2]1[C:7]([F:8])=[C:6]([S:9][C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:21])[N:17]([CH3:20])[CH2:18][CH3:19])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[NH2:22]

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 516892Sodium BicarbonateHCID 234394082-Chloro-3-fluoro-4-[4-(N-methyl-N-ethylcarbamoyl)phenylsulphanyl]nitrobenzene

Product 1

HCID 234394162-Chloro-3-fluoro-4-[4-(N-methyl-N-ethylcarbamoyl)phenylsulphanyl]anilineYield 100.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-3-fluoro-4-[4-(N-methyl-N-ethylcarbamoyl)phenylsulphanyl]nitrobenzene (Method 81; 650 mg. 1.76 mmol) was heated with stirring at 75° C. for 45 minutes with of iron powder (1.06 g), EtOH (1.2 ml), water (0.5 ml) and 2 drops of conc. HCl. The mixture was then allowed to cool to room temp, made basic with saturated sodium bicarbonate solution, and EtOAc was added. The reaction mixture was filtered through a bed of diatomaceous earth, washing through thoroughly with water and EtOAc. The organic layers were combined and washed with water, dried, filtered and evaporated to dryness to give the title compound (600 mg) as a pale yellow gum. NMR: 1.0 (s, 3H), 2.8 (s, 3H), 3.2 (d, 2H), 6.2 (s, 1H), 7.0 (m, 2H), 7.2 (m, 3H).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through a bed of diatomaceous earth
  3. washwashing through thoroughly with water and EtOAc
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-a0cead772eab4c8e8b30feff7a0342c0
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

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