m-Chloroperbenzoic acid → HCID 53663786, compound

HRID 569016Notes

Reaction equation

HRID 569016 reaction equation
[CH2:1]([O:4][C@@H:5]1[C@H:9]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[S:8][C:7]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:6]1=2)[CH:2]=[CH2:3].ClC1C=C(C=CC=1)C(OO)=[O:26]>C(Cl)Cl>[CH2:1]([O:4][C@@H:5]1[C@H:9]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[S:8](=[O:26])[C:7]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:6]1=2)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54232580HCID 54232580, compound

Product 1

HCID 53663786HCID 53663786, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 21.7 g. (70.7 mmole) of (±)-cis-3-allyloxy-6-chloro-2,3-dihydro-2-(1H-1-imidazolylmethyl) benzo[b]thiophene in 500 mL of CH2Cl2 and cool the solution to 0°-5°. Added 14.6 g (70.7 mmole) of m-chloroperoxybenzoic acid (tech. 80-85%) and stir the reaction mixture at 0°-5° for 1 hour. Extract the reaction mixture with 500 mL of 5% aqueous NaHCO3 followed by 500 mL of H2O. Dried the CH2Cl2 layer over anhydrous MgSO4 and concentrate it to give (±)-cis-3-allyloxy-6-chloro-2,3-dihydro-2-(1H-1-imidazolylmethyl)benzo[b]thiophene-1-oxide, a gum, m/e 322.

Workup

  1. dissolutionDissolve 21.7 g
  2. extractionExtract the reaction mixture with 500 mL of 5% aqueous NaHCO3
  3. dry with materialDried the CH2Cl2 layer over anhydrous MgSO4
  4. concentrationconcentrate it

Sources & evidence

ORD record
ord-7da62c98562e4aabaee87bc6d051bc0c
Source dataset
uspto-grants-1988_03
Patent number
US04731364

Reaction notes

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