Ammonium iodide → 2'-amino-1'-benzyl-2-bromo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4'-imidazol]-5'(1'H)-one

HRID 590529

反応式

HRID 590529 の反応式
[CH2:1]([N:8]1[C:12](=[O:13])[C:11]2([C:21]3[CH:20]=[C:19]([Br:22])[S:18][C:17]=3[CH2:16][CH2:15][CH2:14]2)[N:10]=[C:9]1SCC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[NH4+:32]>N.CO>[NH2:32][C:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:12](=[O:13])[C:11]2([C:21]3[CH:20]=[C:19]([Br:22])[S:18][C:17]=3[CH2:16][CH2:15][CH2:14]2)[N:10]=1

参加物

4

反応物 2

HCID 25487Ammonium iodideHCID 900705381'-benzyl-2'-(benzylthio)-2-bromo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4'-imidazol]-5'(1'H)-one

生成物 1

HCID 900705412'-amino-1'-benzyl-2-bromo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4'-imidazol]-5'(1'H)-one収率 41%

試薬・触媒・溶媒 1

HCID 21705897Ammonia methanol溶媒

反応条件

温度
90 °C

実験手順

1′-Benzyl-2′-(benzylthio)-2-bromo-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4′-imidazol]-5′(1′H)-one (0.25 g, 0.5 mmol) and ammonium iodide (0.43 g, 3 mmol) were suspended in 7 N NH3/methanol solution (10 mL). The mixture was heated at 90° C. for 18 hr. The solution was concentrated in vacuo and the crude residue partitioned between water and dichloromethane. The product was extracted into dichloromethane (×3), the organic extracts were combined, dried (MgSO4) and concentrated in vacuo. The crude residue was purified on silica gel using 7 N NH3/methanol in dichloromethane (1:9) to afford the title compound as a foam (80 mg, 41%).

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. customthe crude residue partitioned between water and dichloromethane
  3. extractionThe product was extracted into dichloromethane (×3)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified on silica gel using 7 N NH3/methanol in dichloromethane (1:9)

出典と根拠

ORDレコード
ord-2488d9338b8c43bdb343adee1b9ce72c
出典データセット
uspto-grants-2016_01
特許番号
US09233982B2

関連ノート

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