Benzyl Bromide → 3-benzyl-2-[(4-chlorophenyl)imino]-2,3-dihydro-4H-pyrido[3,2-e]-1,3-thiazin-4-one

HRID 367125

반응식

HRID 367125 반응식
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([NH:6][C:7]2[S:8][C:9]3[N:17]=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[N:12]=2)=[CH:4][CH:3]=1.[H-].[Li+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([N:12]1[C:11](=[O:13])[C:10]2[CH:14]=[CH:15][CH:16]=[N:17][C:9]=2[S:8][C:7]1=[N:6][C:5]1[CH:18]=[CH:19][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

4

반응물 3

HCID 7498Benzyl BromideHCID 62714Lithium hydrideHCID 42920704H-Pyrido[3,2-e]-1,3-thiazin-4-one, 2-[(4-chlorophenyl)amino]-

생성물 1

HCID 232876053-benzyl-2-[(4-chlorophenyl)imino]-2,3-dihydro-4H-pyrido[3,2-e]-1,3-thiazin-4-one수율 73%

실험 절차

The reaction procedure of Example 11 was followed except that 900 mg (2.69 mmol) of 2-(4-chloroanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one, 24 mg of lithium hydride and 507 mg of benzyl bromide were used. The resulting residue was then purified through silica gel column chromatography (eluant: chloroform) to obtain 746 mg of 3-benzyl-2-[(4-chlorophenyl)imino]-2,3-dihydro-4H-pyrido[3,2-e]-1,3-thiazin-4-one (65%, recrystallized from a mixture of ether and hexane) as a low polarity substance and 163 mg of 2-[N-benzyl-N-(4-chlorophenyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one (14%, recrystallized from ether) as a high polarity substance.

후처리

  1. customThe reaction procedure of Example 11
  2. customThe resulting residue was then purified through silica gel column chromatography (eluant: chloroform)

출처 및 근거

ORD 기록
ord-a312ff36c15048959046b4250273dbac
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06133258

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