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

HRID 343393

반응식

HRID 343393 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-902b1ac132304cba9eca5e2dcd403769
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05861401

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