3-Aminopyridine → (RS)-3-(Pyrid-3-ylimino)-9,9a-dihydrothiazolo[3,4-a]indole

HRID 262119ノート

反応式

HRID 262119 の反応式
[I-].CS[C:4]1[S:5][CH2:6][CH:7]2[CH2:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N+:8]=12.[NH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1>N1C=CC=CC=1>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([N:16]=[C:4]2[N:8]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[CH2:15][CH:7]3[CH2:6][S:5]2)[CH:18]=1

参加物

4

反応物 2

HCID 100093-AminopyridineHCID 21320148(RS)-3-Methylthio-9,9a-dihydrothiazolo[3,4-a]indolium iodide

生成物 1

HCID 21320150(RS)-3-(Pyrid-3-ylimino)-9,9a-dihydrothiazolo[3,4-a]indole収率 76.5%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

(RS)-3-Methylthio-9,9a-dihydrothiazolo[3,4-a]indolium iodide (14.0 g) is added to a solution of 3-aminopyridine (4.5 g) in pyridine (150 cc). The suspension gradually passes into solution. After 24 hours at a temperature of about 20° C., the mixture is concentrated to dryness under reduced pressure (25 mm Hg) at 50° C. The residue is dissolved in a mixture of methylene chloride (500 cc) and 2 N aqueous sodium hydroxide solution (150 cc). The organic phase is decanted, washed with water (200 cc), dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (40 mm Hg) at 40° C. The residue obtained is recrystallised from absolute ethanol (40 cc). (RS)-3-(Pyrid-3-ylimino)-9,9a-dihydrothiazolo[3,4-a]indole (8.2 g), melting at 131° C., is obtained.

後処理

  1. concentrationthe mixture is concentrated to dryness under reduced pressure (25 mm Hg) at 50° C
  2. dissolutionThe residue is dissolved in a mixture of methylene chloride (500 cc) and 2 N aqueous sodium hydroxide solution (150 cc)
  3. customThe organic phase is decanted
  4. washwashed with water (200 cc)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (40 mm Hg) at 40° C
  8. customThe residue obtained
  9. customis recrystallised from absolute ethanol (40 cc)

出典と根拠

ORDレコード
ord-ae68dcc0bca14c06a61108bc3106b710
出典データセット
uspto-grants-1979_05
特許番号
US04153699

反応ノート

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