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

HRID 1732611Notes

Reaction equation

HRID 1732611 reaction equation
C[O-].[Na+].Cl.[NH2:5][CH2:6][C:7](=O)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N+:16]([CH:19]=[C:20](SC)[S:21]([CH3:23])=O)([O-:18])=[O:17]>CO>[CH3:23][S:21][C:20]1[NH:5][CH:6]=[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:19]=1[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 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 887MethanolSolvent2×

Procedure

A solution of sodium methoxide (sodium (1.9g, 0.084 mol) dissolved in methanol (100 ml)) and a solution of 1-amino-3-phenylpropan-2-one hydrochloride (7.9g, 0.042 mol) in methanol (100 ml) were simultaneously added dropwise, to a stirred solution of 1-nitro-2-methylthio-2-methylsulphinyl-ethylene (7.7g, 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 (2.95g, 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-b65253d699aa42829a9f33a47888422d
Source dataset
uspto-grants-1980_12
Patent number
US04238494

Reaction notes

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