Disulfide, bis(3-nitrophenyl) → HCID 13044799, compound

HRID 1156377Notes

Reaction equation

HRID 1156377 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]Cl)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Cl:12]Cl.[N+](C1C=C(SSC2C=CC=C([N+]([O-])=O)C=2)C=CC=1)([O-])=O.S(Cl)Cl.[CH:37]([S:39]([C:42]1[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=1)(=[O:41])=[O:40])=[CH2:38]>C(Cl)(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([S:10][CH:37]([S:39]([C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)(=[O:41])=[O:40])[CH2:38][Cl:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 10842Disulfide, bis(3-nitrophenyl)HCID 24526ChlorineHCID 25353Sulfur dichlorideHCID 79665Benzene, 1-(ethenylsulfonyl)-4-methyl-HCID 156206861-(Chlorosulfanyl)-3-nitrobenzene

Product 1

HCID 13044799HCID 13044799, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of 0.642 mole of m-nitrobenzenesulfenyl chloride in enough carbon tetrachloride to make 1060 ml was prepared by passing chlorine for 6.5 hours into a solution of 99 g (0.321 mole) of bis(m-nitrophenyl)disulfide in 1 liter of carbon tetrachloride at 45° C. One-quarter of this solution (265 ml, equivalent to 0.161 mole of the sulfenyl chloride) was treated with 29.2 g (0.160 mole) of p-tolyl vinyl sulfone. Upon standing for several weeks crystals separated. Filtration gave 18 g (30%) of crude product m.p. 92°-101°. Recrystallization from 30 ml of ethyl acetate gave pure material m.p. 103.5°-104.5°.

Workup

  1. customwas prepared
  2. customfor 6.5 hours
  3. customat 45° C
  4. waitUpon standing for several weeks
  5. customcrystals separated
  6. filtrationFiltration
  7. customgave 18 g (30%) of crude product m.p. 92°-101°
  8. customRecrystallization from 30 ml of ethyl acetate

Sources & evidence

ORD record
ord-ca90ad2d36bf456aab287682b4124388
Source dataset
uspto-grants-1982_06
Patent number
US04335142

Reaction notes

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