Ethanethiol → 2-Chloro-1-[3-(ethyldisulfanyl)-4-nitrophenoxy]-4-(trifluoromethyl)benzene

HRID 485619Notes

Reaction equation

HRID 485619 reaction equation
[CH2:1]([SH:3])[CH3:2].C(N(CC)CC)C.[Cl:11][C:12]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:13]=1[O:14][C:15]1[CH:16]=[C:17]([S:24]Cl)[C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1>CCOCC>[CH2:1]([S:3][S:24][C:17]1[C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=[C:15]([O:14][C:13]2[CH:26]=[CH:27][C:28]([C:30]([F:31])([F:32])[F:33])=[CH:29][C:12]=2[Cl:11])[CH:16]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 8471TriethylamineHCID 13246608HCID 13246608, compound

Product 1

HCID 132466102-Chloro-1-[3-(ethyldisulfanyl)-4-nitrophenoxy]-4-(trifluoromethyl)benzeneYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.62 parts by weight of ethanethiol and 2.6 parts by weight of triethylamine were added simultaneously to a solution of 10 parts by weight of 3-(2'-chloro-4'-trifluoromethylphenoxy)-6-nitrobenzenesulfenyl chloride in 100 parts by volume of absolute ether, and stirring was continued for a further 2 hours at room temperature. The reaction mixture was filtered, and the filtrate was extracted with dilute aqueous hydrochloric acid and water, dried over magnesium sulfate, filtered, and evaporated down under reduced pressure. 8 parts by weight (98% yield) of 3-(2'-chloro-4'-trifluoromethylphenoxy)-6-nitrophenyl ethyl disulfide of refractive index nD25 : 1.6067 were obtained (compound No. 4).

Workup

  1. filtrationThe reaction mixture was filtered
  2. extractionthe filtrate was extracted with dilute aqueous hydrochloric acid and water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-ca61ce8ca4cc42738951e2ec4ebfa32e
Source dataset
uspto-grants-1985_08
Patent number
US04537621

Reaction notes

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