4,6-Dichloro-n-methylpyrimidin-2-amine → 4-chloro-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide

HRID 378286

反応式

HRID 378286 の反応式
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][CH3:10])[N:3]=1.[K+].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH-:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1>CN1CCCC1=O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([S:19]([NH:22][C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][CH3:10])[N:3]=2)(=[O:20])=[O:21])=[CH:17][CH:18]=1

参加物

4

反応物 2

HCID 2598804,6-Dichloro-n-methylpyrimidin-2-amineHCID 1317213224-Chloro-benzenesulfonamide potassium salt

生成物 1

HCID 193535554-chloro-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide収率 85%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

0.39 g (0.0022 mol) of (4,6-dichloro-pyrimidin-2-yl)-methylamine and 1.0 g (0.0044 mol) of 4-chloro-benzene-sulfonamide potassium salt were stirred in 10 ml of 1-methyl-2-pyrrolidone at 150° C. for 8 hours. Then, the solvent was distilled off in a high vacuum, the residue was partitioned in ethyl acetate/water and extracted. The aqueous phase was saturated with sodium chloride, evaporated briefly in a vacuum, made acid with 4N HCl and extracted with dichloromethane. The two extracts were combined and chromatographed over silica gel with cyclohexane/ethyl acetate 1:1 as the eluent. There was obtained 0.62 g (85%) of 4-chloro-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide as white crystals. m.p. 196-198° C.

後処理

  1. distillationThen, the solvent was distilled off in a high vacuum
  2. customthe residue was partitioned in ethyl acetate/water
  3. extractionextracted
  4. customevaporated briefly in a vacuum
  5. extractionextracted with dichloromethane
  6. customchromatographed over silica gel with cyclohexane/ethyl acetate 1:1 as the eluent

出典と根拠

ORDレコード
ord-94ca1704d3754db286060055fdd4c10c
出典データセット
uspto-grants-2000_02
特許番号
US06030976

関連ノート

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