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5-Amino-3-ethoxymethylisoquinoline → (S)-3-[(3-Ethoxymethylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline

HRID 1577079
ノート
印刷プレビュー

反応式

HRID 1577079 の反応式
[I-].CS[C:4]1[S:5][CH2:6][C@@H:7]2[CH2:16][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9][N+:8]=12.[NH2:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[C:21]([CH2:28][O:29][CH2:30][CH3:31])[N:22]=[CH:23]2>N1C=CC=CC=1>[CH2:30]([O:29][CH2:28][C:21]1[N:22]=[CH:23][C:24]2[C:19]([CH:20]=1)=[C:18]([N:17]=[C:4]1[N:8]3[CH2:9][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[CH2:16][C@H:7]3[CH2:6][S:5]1)[CH:27]=[CH:26][CH:25]=2)[CH3:31]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 128748535-Amino-3-ethoxymethylisoquinolineHCID 12874874(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide

生成物 1

HCID 12874877(S)-3-[(3-Ethoxymethylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline収率 67.4%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
20 °C

実験手順

(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide (7.2 g) is added to a solution of 5-amino-3-ethoxymethylisoquinoline (4.1 g) in pyridine (150 cc). The suspension is stirred for 24 hours at a temperature of about 20° C. The insoluble material gradually dissolves. The solution is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 60° C. The residue is dissolved in a mixture of methylene chloride (100 cc) and N sodium hydroxide solution (100 cc). The organic phase is decanted, washed with water (50 cc), dried over magnesium sulphate and filtered and the filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is recrystallised from isopropyl alcohol (80 cc). (S)-3-[(3-Ethoxymethylisoquinol-5-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinoline (5.2 g) is thus obtained in the form of a pale yellow solid melting at 88° C.

後処理

  1. dissolutionThe insoluble material gradually dissolves
  2. concentrationThe solution is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 60° C
  3. dissolutionThe residue is dissolved in a mixture of methylene chloride (100 cc) and N sodium hydroxide solution (100 cc)
  4. customThe organic phase is decanted
  5. washwashed with water (50 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe filtrate is evaporated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  9. customThe residue is recrystallised from isopropyl alcohol (80 cc)

出典と根拠

ORDレコード
ord-a6643c9ba35f4972bf8b5415f1331b31
出典データセット
uspto-grants-1981_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04287197

反応ノート

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