Hydrochloric Acid → N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide

HRID 343394ノート

反応式

HRID 343394 の反応式
Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].[CH3:9][O:10][C:11]1[C:12]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[I:28])(=[O:21])=[O:20])=[N:13][CH:14]=[C:15]([CH3:17])[N:16]=1.C(N(CC)CC)C.Cl>ClCCl.N1C=CC=CC=1>[CH2:5]([O:4][C:2]([N:18]([C:12]1[C:11]([O:10][CH3:9])=[N:16][C:15]([CH3:17])=[CH:14][N:13]=1)[S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[I:28])(=[O:21])=[O:20])=[O:3])[CH:6]([CH3:8])[CH3:7]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 10173047N-(3-Methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide

生成物 1

HCID 18704832N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

Isobutyl chloroformate (0.58 ml) was added dropwise to a stirred solution of N-(3-methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide (1.65 g), triethylamine (0.57 ml) and pyridine (0.16 ml) in dichloromethane (30 ml) under an atmosphere of argon. The mixture was stirred for 2 hours and then 2M hydrochloric acid (20 ml) was added. The organic layer was separated, washed with water (20 ml) and saturated sodium chloride solution (20 ml) and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:4 v/v), to give N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide (2.0 g) as a gum; 1H NMR (d6 -DMSO): 0.7 (d,2H), 1.6-1.8 (m,1H), 2.5 (s,3H), 3.9 (d,2H), 4.0 (s,3H), 7.4 (dt,1H), 7.7 (dt,1H), 8.15 (s,1H), 8.2 (dd,1H), 8.35 (dd,1H).

後処理

  1. customThe organic layer was separated
  2. washwashed with water (20 ml) and saturated sodium chloride solution (20 ml)
  3. dry with materialdried (MgSO4)
  4. customVolatile material was removed by evaporation
  5. customthe residue was purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (1:4 v/v)

出典と根拠

ORDレコード
ord-22c4bf0bfd5748eaa05ae2fdab7a02fb
出典データセット
uspto-grants-1999_01
特許番号
US05861401

反応ノート

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