m-Chloroperbenzoic acid → HCID 19866677, compound

HRID 232082Notes

Reaction equation

HRID 232082 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([S:13][C:14]3[NH:18][C:17]4[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=4[N:15]=3)[CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:31])C=1>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([S:13]([C:14]3[NH:15][C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=3)=[O:31])[CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19866700HCID 19866700, compound

Product 1

HCID 19866677HCID 19866677, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of step (b) above (390 mg) in ethyl acetate (20 ml) was cooled to -5° and treated with m-chloroperbenzoic acid (273 mg of 85% pure material). The temperature was allowed to rinse to ambient. The reaction mixture was then diluted with ethyl acetate and methylene chloride, and then washed with sodium bisulphite solution, sodium bicarbonate solution and brine. The solution was dried and evaporated. Column chromatography (SiO2 /ethyl acetate) gave the title compound 140 mg, mp 178°-9° (d).

Workup

  1. washto rinse
  2. additionThe reaction mixture was then diluted with ethyl acetate and methylene chloride
  3. washwashed with sodium bisulphite solution, sodium bicarbonate solution and brine
  4. customThe solution was dried
  5. customevaporated

Sources & evidence

ORD record
ord-d242d943a19e4c0c95b6ad353b8cf6ba
Source dataset
uspto-grants-1989_07
Patent number
US04851419

Reaction notes

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