2-Iodobenzene-1-sulfonyl chloride → N-(3-Methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide

HRID 343393ノート

反応式

HRID 343393 の反応式
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[NH2:12][C:13]1[C:18]([O:19][CH3:20])=[N:17][C:16]([CH3:21])=[CH:15][N:14]=1>N1C=CC=CC=1>[CH3:20][O:19][C:18]1[C:13]([NH:12][S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[I:1])(=[O:10])=[O:9])=[N:14][CH:15]=[C:16]([CH3:21])[N:17]=1

参加物

4

反応物 2

HCID 6274002-Iodobenzene-1-sulfonyl chlorideHCID 107018943-Methoxy-5-methyl-2-pyrazinamine

生成物 1

HCID 10173047N-(3-Methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide収率 44.4%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
70 °C

実験手順

2-Iodobenzenesulphonyl chloride (obtained as described in J Org Chem, 1977, 42, 3265) (12.1 g) was added to a solution of 2-amino-3-methoxy-5-methylpyrazine (5.6 g) in pyridine (100 ml) and the solution was heated at 70° C. for 8 hours. Volatile material was removed by evaporation and water (200 ml) was added to the residue. The mixture was extracted with ethyl acetate (2×200 ml) and the extracts were washed with 2M hydrochloric acid (200 ml) and water (200 ml). The extracts were dried (MgSO4) and the solvent was removed by evaporation. The residue was triturated with ether to give N-(3-methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamide (7.2 g), m.p. 136°-138° C.; 1H NMR (d6 -DMSO): 2.3 (s,3H), 3.9 (s,3H), 7.3 (dt,1H), 7.5-7.65 (m,2H), 8.05-8.15 (m,2H), 10.7-10.8 (br s, 1H).

後処理

  1. customVolatile material was removed by evaporation and water (200 ml)
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with ethyl acetate (2×200 ml)
  4. washthe extracts were washed with 2M hydrochloric acid (200 ml) and water (200 ml)
  5. dry with materialThe extracts were dried (MgSO4)
  6. customthe solvent was removed by evaporation
  7. customThe residue was triturated with ether

出典と根拠

ORDレコード
ord-902b1ac132304cba9eca5e2dcd403769
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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