盐酸 → N-(1,1-Dimethylethyl)-1-methyl-2-(methylthio)-1H-pyrrole-3-sulfonamide

HRID 1081237笔记

反应方程式

HRID 1081237 反应方程式
[CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].C([Li])CCC.[CH3:20][S:21]SC.Cl>C1COCC1>[CH3:4][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[S:21][CH3:20])(=[O:8])=[O:7])([CH3:1])[CH3:3]

参与物

6

反应物 4

HCID 313盐酸HCID 12232二甲基二硫HCID 19693811N-(1,1-Dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamideHCID 178418339正丁基锂

产物 1

HCID 19693814N-(1,1-Dimethylethyl)-1-methyl-2-(methylthio)-1H-pyrrole-3-sulfonamide收率 58.8%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

反应条件

温度
-78 °C

实验过程

To a solution of 6.48 g (30 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL THF under nitrogen atmosphere cooled to -78° C. was added dropwise at such a rate as to keep the temperature below -65° C. 25.52 mL (61.5 mmol) 2.41M n-butyllithium in hexanes. The reaction was stirred at -78° C. for ca. 30 minutes. To the reaction mixture was added 2.97 mL (33 mmol) of dimethyldisulfide in one portion and the resulting reaction mixture was allowed to warm to room temperature and stir for ca. 1.5 hours. The reaction mixture was cooled to 0° C. and acidified with 1N HCl. The THF phase was separated washed with brine, dried (MgSO4) and concentrated in vacuo. The crude residue was chromatographed on silica (20% ethyl acetate/80% hexanes) affording 4.63 g of the title compound as an off white solid, m.p. 116°-119° C.

后处理

  1. additionwas added dropwise at such a rate as
  2. customthe temperature below -65° C
  3. customthe resulting reaction mixture
  4. temperatureto warm to room temperature
  5. stirringstir for ca. 1.5 hours
  6. temperatureThe reaction mixture was cooled to 0° C.
  7. customThe THF phase was separated
  8. washwashed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customThe crude residue was chromatographed on silica (20% ethyl acetate/80% hexanes)

来源与证据

ORD记录
ord-31047b9f15c44866bc8f9dfa791fd7b4
来源数据集
uspto-grants-1996_12
专利号
US05585328

反应笔记

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