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

HRID 5828

反応式

HRID 5828 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒

実験手順

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-chlorophenyl)-1H-naphtho-[2,1-b][1,4]thiazin-2(3H)-one (44.45 g, yield 82.6%) as crystals.

後処理

  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

出典と根拠

ORDレコード
ord-d1e1ce17b0b34812b37a771e23bf789c
出典データセット
uspto-grants-1993_09
特許番号
US05246929

関連ノート

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