Chloroform → N-(3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]1,2-thiazine-3-carboxamide-1,1-dioxide

HRID 1730578ノート

反応式

HRID 1730578 の反応式
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][C:10]3[C:15]([C:6]=2[S:5](=[O:17])(=[O:16])[NH:4][C:3]=1[C:18]([NH2:20])=[O:19])=[CH:14][CH:13]=[CH:12][CH:11]=3.[CH:21]([Cl:24])(Cl)Cl.[H][H]>[Pd].CO>[Cl:24][C:21]1[CH:18]=[C:3]([NH:20][C:18]([C:3]2[NH:4][S:5](=[O:17])(=[O:16])[C:6]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=[CH:8][C:7]=3[C:2]=2[OH:1])=[O:19])[CH:2]=[CH:7][CH:6]=1

参加物

6

反応物 3

HCID 6212ChloroformHCID 681429134-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 54695941N-(3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]1,2-thiazine-3-carboxamide-1,1-dioxide収率 57%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A solution of 490 mgm (1 millimol) of 2-benzyl-N-3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide in 100 ml of a mixture of chloroform and methanol (2:1) was hydrogenated in the presence of 500 mgm of a palladium-on-charcoal catalyst (10%) at a hydrogen pressure of 3 atmospheres for 10 hours. The reaction mixture was then filtered, and the catalyst left on the filter was copiously washed with hot chloroform. The combined filtrates were evaporated, and the residue was purified by columnchromatography (silicagel particle size 0.2-0.5 mm), using chloroform/methanol (20:1) as the eluant. 230 mgm (57% of theory) of N-(3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]1,2-thiazine-3-carboxamide-1,1-dioxide, m.p. 262° C (decomp.), were obtained.

後処理

  1. filtrationThe reaction mixture was then filtered
  2. waitthe catalyst left on the filter
  3. washwas copiously washed with hot chloroform
  4. customThe combined filtrates were evaporated
  5. customthe residue was purified by columnchromatography (silicagel particle size 0.2-0.5 mm)

出典と根拠

ORDレコード
ord-a644cc8250bf4c7cb2cccf8c5d6c32d8
出典データセット
uspto-grants-1976_11
特許番号
US03992535

反応ノート

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