Water → HCID 23350165, compound

HRID 2058277Notes

Reaction equation

HRID 2058277 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][C:16]([N+:23]([O-:25])=[O:24])=[CH:15][C:14]=1[N+:26]([O-:28])=[O:27].[Cl:29][C:30]([SH:33])([Cl:32])[Cl:31].O.ClCCCC.CCCCCC>O1CCCC1>[Cl:29][C:30]([Cl:32])([Cl:31])[S:33][N:12]([C:3]1[CH:4]=[C:5]([C:8]([F:10])([F:9])[F:11])[CH:6]=[CH:7][C:2]=1[Cl:1])[C:13]1[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][C:16]([N+:23]([O-:25])=[O:24])=[CH:15][C:14]=1[N+:26]([O-:28])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 6390TrichloromethanethiolHCID 12797626FentrifanilHCID 23000051HCID 23000051, compound

Product 1

HCID 23350165HCID 23350165, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.6 g, 57% mineral oil), washed free of mineral oil with hexane under a nitrogen atmosphere, is slurried in 25 ml of anhydrous tetrahydrofuran and cooled to 0°. A solution of 2-chloro-N-[2,4-dinitro-6-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-benzenamine (4.3 g, 0.010 mole) in 25 ml of anhydrous tetrahydrofuran is then added dropwise with stirring at 0°. When the addition is complete, the solution is allowed to warm to ambient temperature and stirred for one hour. Perchloromethyl mercaptan (1.9 g, 0.010 mole) is then added and stirring is continued for two hours. The reaction mixture is then poured into water, extracted with methylene chloride, dried over anhydrous magnesium sulfate and stripped under vacuum to afford an orange resin. Chromatography on silica gel utilizing 1-chlorobutane/hexane (1:1 by vol) as the eluent affords 3.5 g of 1,1,1-trichloro-N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethyl)phenyl]methanesulfenamide as a yellow oil which crystallizes on standing, m.p. 134°-137°.

Workup

  1. washSodium hydride (0.6 g, 57% mineral oil), washed free of mineral oil with hexane under a nitrogen atmosphere
  2. temperaturecooled to 0°
  3. additionWhen the addition
  4. stirringstirred for one hour
  5. stirringstirring
  6. extractionextracted with methylene chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customto afford an orange resin

Sources & evidence

ORD record
ord-2911155b851646088d1ca56378d7c876
Source dataset
uspto-grants-1980_07
Patent number
US04215145

Reaction notes

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