1-Amino-2-naphthalenethiol → 3-(4-chlorophenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one

HRID 1198440

반응식

HRID 1198440 반응식
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[SH:12].[BH4-].[Na+].C([O-])(=O)C.[Na+].Br[CH:21]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:22](OC)=[O:23]>C(O)C.C(O)(=O)C>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH:21]2[S:12][C:3]3[CH:4]=[CH:5][C:6]4[C:11]([C:2]=3[NH:1][C:22]2=[O:23])=[CH:10][CH:9]=[CH:8][CH:7]=4)=[CH:27][CH:28]=1

참가 물질

7

반응물 4

HCID 1133141-Amino-2-naphthalenethiolHCID 517045Sodium AcetateHCID 4311764Sodium borohydrideHCID 10777987Methyl 2-bromo-2-(4-chlorophenyl)acetate

생성물 1

HCID 189844403-(4-chlorophenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one수율 86%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 702Ethanol용매

실험 절차

To a solution of 1-amino-2-naphthalenethiol (27.81 g) in ethanol (500 ml) is added sodium borohydride (11.35 g) at room temperature. The mixture is stirred for 20 minutes, and thereto is added dropwise acetic acid (200 ml) and is further added sodium acetate (24.6 g). To the mixture is further added dropwise methyl α-bromo-4-chlorophenylacetate (46.8 g), and the mixture is sitrred at room temperature under argon overnight. The reaction mixture is poured into ice water and the resulting precipitate is separated by filtration, washed, dried and recrystallized from tetrahydrofuran-n-hexane to give 3-(4-chlorphenyl)-1H-naphtho[2,1-b][1,4]thiazin-2(3H)-one (44.45 g, yield 82.6%) as crystals.

후처리

  1. waitthe mixture is sitrred at room temperature under argon overnight
  2. customthe resulting precipitate is separated by filtration
  3. washwashed
  4. customdried
  5. customrecrystallized from tetrahydrofuran-n-hexane

출처 및 근거

ORD 기록
ord-4e723883002e4d7b86b8bb54c9017582
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05281592

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