N-methyl-2-pyrrolidone → 4-tert-butyl-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide

HRID 1585703ノート

反応式

HRID 1585703 の反応式
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4](CN)[N:3]=1.[K+].[C:12]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH-:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].[CH3:26][N:27]1CCCC1=O>>[C:12]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:27][CH3:26])[N:3]=2)(=[O:23])=[O:24])=[CH:18][CH:17]=1)([CH3:15])([CH3:13])[CH3:14]

参加物

4

反応物 3

HCID 13387N-methyl-2-pyrrolidoneHCID 19353478(4,6-Dichloropyrimidin-2-yl)methanamineHCID 131721323HCID 131721323、化合物

生成物 1

HCID 193535354-tert-butyl-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide収率 73%

実験手順

0.39 g (0.0022 mol) of (4,6-dichloro-pyrimidin-2-yl)methyl-amine and 1.1 g (0.0044 mol) of 4-tert-butyl-benzenesulfonamide 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, de-gassed in a vacuum and made acid with 4N HCl, with a precipitate separating. The mixture was suction filtered, the extract and the solid were combined and chromatographed over silica gel with cyclohexane/ethyl acetate 2:1 as the eluent. The product was recrystallized from ethyl acetate/n-hexane. There was obtained 0.57 g (73%) of 4-tert-butyl-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide as white crystals; m.p.: 118-137° C. (dec.).

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. customde-gassed in a vacuum
  5. customwith a precipitate separating
  6. filtrationfiltered
  7. extractionthe extract
  8. customchromatographed over silica gel with cyclohexane/ethyl acetate 2:1 as the eluent
  9. customThe product was recrystallized from ethyl acetate/n-hexane

出典と根拠

ORDレコード
ord-6bf57a26f8fa4055bf1e67431f063aa6
出典データセット
uspto-grants-1999_08
特許番号
US05939451

反応ノート

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