Acetic Acid → HCID 365395, compound

HRID 2083689Notes

Reaction equation

HRID 2083689 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]Cl)=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[C:13](O)(=O)[CH3:14]>C(OCC)C>[N+:10]([C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[S:8][C:14]1[CH:13]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11])([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 10443590Benzenesulfenyl chloride, 4-chloro-2-nitro-

Product 1

HCID 365395HCID 365395, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 1.37 g. of 3-butenyltributyltin was added 0.89 g. of 4-chloro-2-nitrobenzene sulfenyl chloride dissolved in 20 ml. glacial acetic acid at steam bath temperature. The mixture was then heated on a steam bath for 30 minutes and poured into an ice water bath. The product was taken up in diethyl ether, washed twice with 50 ml. portions of water, twice with 50 ml. portions of saturated sodium bicarbonate and an additional time with 50 ml. of water. The resulting ether layer was separated, dried over magnesium sulfate and filtered. The solvent was removed on a rotary evaporator and the concentrate analyzed by proton nmr. The product proved to be cyclopropylcarbinyl 2-nitro-4-chlorophenyl sulfide.

Workup

  1. temperatureThe mixture was then heated on a steam bath for 30 minutes
  2. additionpoured into an ice water bath
  3. washwashed twice with 50 ml
  4. customThe resulting ether layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-f99637a3d4ff49a5a86a7e7bb5f605fe
Source dataset
uspto-grants-1978_04
Patent number
US04086280

Reaction notes

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