Methyl iodide → N-(1,1-Dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide

HRID 2259176

反応式

HRID 2259176 の反応式
[CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][NH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].CI.[CH3:16]C(C)([O-])C.[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:4][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:16])[CH:10]=1)(=[O:8])=[O:7])([CH3:1])[CH3:3]

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 19693846N-(tert-Butyl)-1H-pyrrole-3-sulfonamideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 19693811N-(1,1-Dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

A solution of N-(1,1-dimethylethyl)-1H-pyrrole-3-sulfonamide 9 g (0.044 mol) in 90 mL N,N-dimethylforamide was cooled to 15° C. under a nitrogen atmosphere. To this was added 3.2 mL (0.053 mol) of methyl iodide followed by 5.43 g (0.048 mol) of potassium t-butoxide. The mixture was warmed at ca. 60° C. for 2 hours then allowed to cool to room temperature and stirred for ca. 2 hours. The reaction mixture was diluted with ethyl acetate, washed three times with 1N HCl, once with brine, dried (MgSO4) and evaporated to an oily solid which was triturated with 5% diethyl ether/95% hexanes affording 6 g of the title compound as a beige solid, m.p. 134°-135° C. 1H NMR (CDCl3, 200 MHz.) δ: 7.11(s,1H), 6.59(d,1H), 6.41(d,1H), 4.32(bs,1H), 3.67(s,3H), 1.26(s,9H).

後処理

  1. temperatureto cool to room temperature
  2. washwashed three times with 1N HCl
  3. dry with materialonce with brine, dried (MgSO4)
  4. customevaporated to an oily solid which
  5. customwas triturated with 5% diethyl ether/95% hexanes affording 6 g of the title compound as a beige solid, m.p. 134°-135° C

出典と根拠

ORDレコード
ord-2958c153c3924c6abfce5f1225a2a15a
出典データセット
uspto-grants-1995_12
特許番号
US05472933

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