m-Chloroperbenzoic acid → HCID 14821696, compound

HRID 2352677Notes

Reaction equation

HRID 2352677 reaction equation
[CH3:1][N:2]([CH3:17])[C:3](=[O:16])[O:4][CH2:5][CH:6]=[C:7]([F:15])[S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].ClC1C=CC=C(C(OO)=[O:26])C=1>C(Cl)Cl>[CH3:17][N:2]([CH3:1])[C:3](=[O:16])[O:4][CH2:5]/[CH:6]=[C:7](\[F:15])/[S:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:26]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54091611HCID 54091611, compound

Product 1

HCID 14821696HCID 14821696, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the above carbamate is added a solution of m-chloroperbenzoic acid (431 mg, 2.5 mmol) in 10 ml of methylene chloride. After 15 min, the reaction mixture is extracted with KHCO3 and Na2SO3 and stripped. The product is purified by prep. TLC eluting with ethyl acetate (neat). The upper band is collected to give (E)-3-fluoro-3-hexylsulfinyl-2-propenyl dimethylcarbamate (cpd. 28, Table A).

Workup

  1. extractionthe reaction mixture is extracted with KHCO3 and Na2SO3
  2. customThe product is purified by prep
  3. washTLC eluting with ethyl acetate (neat)
  4. customThe upper band is collected

Sources & evidence

ORD record
ord-6f69991cb8784be095d9e0bc9e278957
Source dataset
uspto-grants-1989_10
Patent number
US04877899

Reaction notes

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