Sodium → 4-Benzyl-2-(methylsulfanyl)-3-nitro-1H-pyrrole

HRID 1065760Notes

Reaction equation

HRID 1065760 reaction equation
C[O-].[Na+].[Na].Cl.[NH2:6][CH2:7][C:8](=O)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N+:17]([CH:20]=[C:21](SC)[S:22]([CH3:24])=O)([O-:19])=[O:18]>CO>[CH3:24][S:22][C:21]1[NH:6][CH:7]=[C:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:20]=1[N+:17]([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 132906721-Amino-3-phenylpropan-2-one--hydrogen chloride (1/1)HCID 544870941-Nitro2-methylthio-2-methylsulphinylethylene

Product 1

HCID 136466304-Benzyl-2-(methylsulfanyl)-3-nitro-1H-pyrroleYield 28.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of sodium methoxide (sodium (1.9 g, 0.084 mol) dissolved in methanol (100 ml) and a solution of 1-amino-3-phenylpropan-2-one hydrochloride (7.9 g, 0.042 mol) in methanol (100 ml) were simultaneously added dropwise, to a stirred solution of 1-nitro-2-methylthio-2-methylsulphinylethylene (7.7 g, 0.042 mol) in methanol. The temperature was maintained at about 60° during the addition, which took 25 minutes. The solvent was then removed in vacuo, and the residual dark red oil was chromatographed on a silica gel column. Elution and recrystallisation with petroleum ether/ethyl acetate (7:3) gave 2-methylthio-3-nitro-4-benzylpyrrole (2.95 g, 28.5%) m.p. 190°-192.5°.

Workup

  1. temperatureThe temperature was maintained at about 60° during the addition, which
  2. customThe solvent was then removed in vacuo
  3. customthe residual dark red oil was chromatographed on a silica gel column
  4. washElution and recrystallisation with petroleum ether/ethyl acetate (7:3)

Sources & evidence

ORD record
ord-d2275e12a42241409482985d7f58c615
Source dataset
uspto-grants-1982_05
Patent number
US04331668

Reaction notes

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