Methyl iodide → 3-[(2-Methyl-1-Imidazolyl)Methyl]-4-Oxo-2,3,4,9-Tetrahydrothiopyrano[2,3-b]Indole

HRID 1086517ノート

反応式

HRID 1086517 の反応式
IC.CN([CH2:6][CH:7]1[CH2:19][S:18][C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8]1=[O:20])=[CH:16][CH:15]=[CH:14][CH:13]=3)C.[CH3:21][C:22]1[NH:23][CH:24]=[CH:25][N:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH3:21][C:22]1[N:23]([CH2:6][CH:7]2[CH2:19][S:18][C:10]3[NH:11][C:12]4[C:17]([C:9]=3[C:8]2=[O:20])=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:24]=[CH:25][N:26]=1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 127492-MethylimidazoleHCID 198261533-[(Dimethylamino)Methyl]-4-Oxo-2,3,4,9-Tetrahydrothiopyrano[2,3-b]Indole

生成物 1

HCID 198261563-[(2-Methyl-1-Imidazolyl)Methyl]-4-Oxo-2,3,4,9-Tetrahydrothiopyrano[2,3-b]Indole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

5.60 ml (0.09 mol) of iodomethane are added to a solution of 23.43 g (0.09 mol) of 3-[(dimethylamino)methyl]-4-oxo-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole (hydrochloride) in 250 ml of dimethylformamide. The mixture is stirred at room temperature for 1 hour, a solution of 22.17 g (0.27 mol) of 2-methylimidazole in 50 ml of dimethylformamide is then added and the reaction medium is thereafter heated to 100° C. for 36 hours. After the mixture is cooled, 500 ml of 2N aqueous sodium carbonate solution are added and the resulting mixture is extracted three times with ethyl acetate. The organic phases are combined, washed with water (200 ml), dried and concentrated under vacuum. The product is chromatographed on silica, eluting with a methylene chloride/ethanol/ammonia solution mixture (92:8:0.5). The residue is recrystallized in acetonitrile.

後処理

  1. temperaturethe reaction medium is thereafter heated to 100° C. for 36 hours
  2. temperatureAfter the mixture is cooled
  3. extractionthe resulting mixture is extracted three times with ethyl acetate
  4. washwashed with water (200 ml)
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customThe product is chromatographed on silica
  8. washeluting with a methylene chloride/ethanol/ammonia solution mixture (92:8:0.5)
  9. customThe residue is recrystallized in acetonitrile

出典と根拠

ORDレコード
ord-210aaedc075d4159888d164a6f6cdbb3
出典データセット
uspto-grants-1991_07
特許番号
US05030646

反応ノート

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