m-Chloroperbenzoic acid → HCID 23464484, compound

HRID 444137Notes

Reaction equation

HRID 444137 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:12][C:7]=2[S:6][C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[NH:3]1.ClC1C=CC=C(C(OO)=[O:29])C=1>C(Cl)(Cl)Cl>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:12][C:7]=2[S:6](=[O:29])[C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[NH:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 13013924HCID 13013924, compound

Product 1

HCID 23464484HCID 23464484, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dissolve 2 gm (0.0071 moles) of the ester of Example 2 in 200 cc of chloroform and 1.396 gm of m-chloroperbenzoic acid and stir at room temperature for 20 minutes. Add successive 100 mg portions of m-chloroperbenzoic acid until thin layer chromatography slows conversion of the starting material. Basify with calcium hydroxide and separate the solids. Chromotograph the solids over silica gel eluting with 30% ethyl acetate in benzene to obtain the title product (yield 870 mg).

Workup

  1. customBasify with calcium hydroxide and separate the solids

Sources & evidence

ORD record
ord-c5adb4d82260472990f07244d8e46a6c
Source dataset
uspto-grants-1981_04
Patent number
US04263207

Reaction notes

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