m-Chloroperbenzoic acid → HCID 178477615, compound

HRID 1534664Notes

Reaction equation

HRID 1534664 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2([S:19][CH2:20][CH3:21])[CH2:18][CH2:17]2)([OH:15])[CH2:9][C:10]2[N:14]=[CH:13][NH:12][N:11]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2([S:19]([CH2:20][CH3:21])=[O:30])[CH2:17][CH2:18]2)([OH:15])[CH2:9][C:10]2[N:14]=[CH:13][NH:12][N:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178477312HCID 178477312, compound

Product 1

HCID 178477615HCID 178477615, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 g (0.0155 mol) of 1-(4-chlorophenyl)-1-[1-(ethylthio)-1-cyclopropyl]-2-(1,2,4-triazol-yl)-1-ethanol (see Example 1) are stirred with 3.3 g of m-chloroperbenzoic acid (80-90% strength) in 40 ml of methylene chloride overnight at room temperature and then for one hour under reflux. Thereafter, the mixture is washed with twice 20 ml of 5% strength aqueous sodium hydroxide solution and twice with water. The organic phase is dried over sodium sulphate and evaporated down in vacuo. The residue is recrystallized from glycol monomethyl ether acetate. 3 g (57% of theory) of 1-(4-chlorophenyl)-1-[1-(ethylsulphinyl)-1-cyclopropyl]-2-(1,2,4-triazol-yl)-1-ethanol of boiling point 185° C. are obtained.

Workup

  1. temperaturefor one hour under reflux
  2. washThereafter, the mixture is washed with twice 20 ml of 5% strength aqueous sodium hydroxide solution and twice with water
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. customevaporated down in vacuo
  5. customThe residue is recrystallized from glycol monomethyl ether acetate

Sources & evidence

ORD record
ord-27e35052dfc64484aae5704591d7171a
Source dataset
uspto-grants-1992_02
Patent number
US05089640

Reaction notes

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