Pyridine → N-[[[4-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]amino]thio]-N-ethylmethanesulphonamide

HRID 652599

Reaction equation

HRID 652599 reaction equation
[S:1](Cl)Cl.[CH2:4]([NH:6][S:7]([CH3:10])(=[O:9])=[O:8])[CH3:5].N1C=CC=CC=1.[Cl:17][C:18]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:19]=1[O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1>C(OCC)C>[Cl:17][C:18]1[CH:31]=[C:30]([C:32]([F:34])([F:33])[F:35])[CH:29]=[CH:28][C:19]=1[O:20][C:21]1[CH:22]=[CH:23][C:24]([NH:25][S:1][N:6]([CH2:4][CH3:5])[S:7]([CH3:10])(=[O:9])=[O:8])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 25353Sulfur dichlorideHCID 5136276N-ethylmethanesulfonamideHCID 104693274-[2-Chloro-4-(trifluoromethyl)phenoxy]aniline

Product 1

HCID 20197941N-[[[4-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]amino]thio]-N-ethylmethanesulphonamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 2.6 g of sulphur dichloride in 15 ml of dry diethyl ether was added over 10 minutes to a stirred solution of 3.1 g of N-ethylmethanesulphonamide in 15 ml of the same solvent, keeping the temperature between 10°-15° by means of external cooling. A solution of 2.0 g of dry pyridine in 15 ml of dry diethyl ether was then added over 15 minutes at the same temperature and the reaction mixture was allowed to warm to room temperature over 1 hour. The resulting suspension was added over 5 minutes to a solution of 7.2 g of 4-[2-chloro-4-(trifluoromethyl)phenoxy]aniline (1A) in 75 ml of dry diethyl ether containing 2.0 g of pyridine, keeping the temperature of the mixture between 5°-10° C. After stirring at 10°-15° for 1 hour, the reaction mixture was washed three times with water, the ether layer was separated, dried (MgSO4), and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel using diethyl ether as eluent, to give 2, as a buff solid m.p.: 98°-101° C.

Workup

  1. custombetween 10°-15°
  2. custombetween 5°-10° C
  3. washthe reaction mixture was washed three times with water
  4. customthe ether layer was separated
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel
  8. customto give 2

Sources & evidence

ORD record
ord-27a9692f225a4eb7b0ba90f692967227
Source dataset
uspto-grants-1987_06
Patent number
US04672139

Linked notes

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