Ethanol → HCID 23439417, compound

HRID 2120379Notes

Reaction equation

HRID 2120379 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:20])[NH:17][CH2:18][CH3:19])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[N+:21]([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:20])[NH:17][CH2:18][CH3:19])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[NH2:21]

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 516892Sodium BicarbonateHCID 23439406HCID 23439406, compound

Product 1

HCID 23439417HCID 23439417, compoundYield 78.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-3-fluoro-4-[4-(N-ethylcarbamoyl)phenylsulphanyl]nitrobenzene (Method 82; 360 mg, 1.02 mmol), iron powder (617 mg), EtOH (0.68 ml), water (0.28 ml) and 1 drop of conc. HCl were heated at 75° C. with stirring for 45 minutes. The mixture was allowed to cool to room temp and then made basic using saturated sodium bicarbonate solution. EtOAc was added and the solution was poured onto a Chem Elut column and eluted with EtOAc to yield the title compound (260 mg) as a pale yellow sticky solid. NMR: 1.1 (t, 3H), 3.2 (q, 2H), 6.1 (s, 1H), 7.0 (q, 2H), 7.2 (q, 1H), 7.7 (t, 2H), 8.3 (d, 1H).

Workup

  1. additionthe solution was poured onto a Chem Elut column
  2. washeluted with EtOAc

Sources & evidence

ORD record
ord-05737ee485804d4ab8ccb68aa8af4608
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

Loading…