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

HRID 1730578노트

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HRID 1730578 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a644cc8250bf4c7cb2cccf8c5d6c32d8
출처 데이터셋
uspto-grants-1976_11
특허 번호
US03992535

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