Acetic Acid → HCID 13646636, compound

HRID 1381005Notes

Reaction equation

HRID 1381005 reaction equation
[CH3:1][S:2][C:3]1[NH:4][CH:5]=[C:6]([CH:11]([CH2:13]C)C)[C:7]=1[N+:8]([O-:10])=[O:9].[OH:15]O.[C:17](O)(=O)[CH3:18]>>[CH3:1][S:2]([C:3]1[NH:4][CH:5]=[C:6]([CH2:11][CH2:13][CH2:17][CH3:18])[C:7]=1[N+:8]([O-:10])=[O:9])=[O:15]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 57057744HCID 57057744, compound

Product 1

HCID 13646636HCID 13646636, compound

Procedure

2-Methylthio-3-nitro-4-b-butylpyrrole (3.7 g) was suspended in glacial acetic acid (50 ml) and 30% hydrogen peroxide (1.62 g) was added. The mixture was heated to 80° for 7 hours, and it was then evaporated to a brown oil. The crude product was purified by column chromatography using silica gel, eluted with benzene and chloroform, to give an oil which crystallized on standing. This was recrystallised from 2-propanol to give 2-methylsulphinyl-3-nitro-4-n-butylpyrrole (1.6 g), m.p 133°-4°.

Workup

  1. temperatureThe mixture was heated to 80° for 7 hours
  2. customit was then evaporated to a brown oil
  3. customThe crude product was purified by column chromatography
  4. washeluted with benzene and chloroform
  5. customto give an oil which
  6. customcrystallized
  7. customThis was recrystallised from 2-propanol

Sources & evidence

ORD record
ord-1168c0f09d5049049562e58a99f67bfa
Source dataset
uspto-grants-1986_04
Patent number
US04584384

Reaction notes

Loading…