m-Chloroperbenzoic acid → HCID 13491910, compound

HRID 46764Notes

Reaction equation

HRID 46764 reaction equation
[CH3:1][CH:2]([S:4][C:5]1[NH:6][C:7]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:9]=1)[CH3:3].ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)Cl>[CH3:3][CH:2]([S:4]([C:5]1[NH:6][C:7]([C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)=[C:8]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[N:9]=1)=[O:32])[CH3:1]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13136580HCID 13136580, compound

Product 1

HCID 13491910HCID 13491910, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The 2-isopropylthioimidazole from Example 9 (11.1 g, 35 mmole) was suspended in 300 ml of methylene chloride and placed in an ice-bath. m-Chloroperbenzoic acid (7.5 g) was added in 100 ml. of methylene chloride over the period of 40 minutes. The solution was stirred for an additional 15 minutes and organic solution extracted with sodium bicarbonate (5%). The aqueous alkaline extract was discarded and the organic layer was dried and evaporated to give a semi-solid which was recrystallized from methylene chloride-ether yielding 7.5 g of a crystalline solid which was further purified by chromatography (alumina). The pure product was obtained from chloroform elution: 180°-181.5°.

Workup

  1. customplaced in an ice-bath
  2. customover the period of 40 minutes
  3. extractionorganic solution extracted with sodium bicarbonate (5%)
  4. extractionThe aqueous alkaline extract
  5. customthe organic layer was dried
  6. customevaporated
  7. customto give a semi-solid which
  8. customwas recrystallized from methylene chloride-ether yielding 7.5 g of a crystalline solid which
  9. customwas further purified by chromatography (alumina)
  10. customThe pure product was obtained from chloroform elution
  11. custom180°-181.5°

Sources & evidence

ORD record
ord-aee7e967ad164d7298374715c10e4de1
Source dataset
uspto-grants-1979_11
Patent number
US04175127

Reaction notes

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