Benzyl Chloride → HCID 10454683、化合物

HRID 2370423

反応式

HRID 2370423 の反応式
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13].[H-].[Na+].[H][H].[CH2:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[CH2:21]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([I:1])=[CH:10][CH:9]=2)[C:5]([CH2:11][C:12]([N:14]([CH3:15])[CH3:16])=[O:13])=[CH:6]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

6

反応物 4

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 102459112-(5-iodo-1H-indol-3-yl)-N,N-dimethyl-acetamideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 10454683HCID 10454683、化合物収率 85%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-(5-Iodo-1H-indol-3-yl)-N,N-dimethyl-acetamide (24.7 g, 75.4 mmol) in DMF (90 mL), under an inert atmosphere sodium hydride (1.91 g 95%, 75.4 mmol) is added which leads to the formation of a pale yellow solution. When the evolution of hydrogen has ceased, benzyl chloride (9.54 g, 75.4 mmol) is added in three portions over a period of 10 minutes. The mixture warms to 60° C., and after stirring for one hour a suspension forms. On the rotavapor, a part of the DMF (about 80 mL) is removed, which leads to crystallization of the product. Water (300 mL) is added, and the crystallized product is triturated at 80° C. for one hour on the rotavapor. The product is filtered off, washed twice with water (200 mL each washing), and dried to give 26.8 g (85%) of the title compound as pale yellow crystals, mp=167-168° C. From the mother liquor, another crop (2.6 g, 8%) is obtained which is also pure. 1H-NMR (DMSO-D6, 300 MHz) δ 3.33, 3.72 (2 s, 3H each, N(CH3)2); 3.72 (s, 2H, CH2CO); 5.34 (CH2Ph); 7.08-7.15, 7.15-7.30 (2 m, 5H, Ph); 7.24 (d, 3J=8.7 Hz, H-7); 7.26 (s, 1H, H-2); 7.32 (dd, 4J=1.3 Hz, H-6); 7.94 (d, 1H, H-4). 13C-NMR (DMSO-D6, 75 MHz) δ 30.90 (CH2CO); 35.72, 37.89 (N(CH3)2); 49.70 (CH2Ph); 83.31 (C-5); 108.61 (C-3); 113.26 (C-2); 127.65 (2 Ph-C); 128.06 (C-6 or Ph C-4); 128.53 (C-4); 129.19 (Ph C-4 or C-6); 129.22 (2 Ph-C); 129.83 (C-7); 131.38 (Ph ipso-C); 135.79 (C-9); 138.67 (C-8); 170.82 (CONMe2).

後処理

  1. customwarms to 60° C.
  2. customOn the rotavapor, a part of the DMF (about 80 mL) is removed
  3. customwhich leads to crystallization of the product
  4. additionWater (300 mL) is added
  5. customthe crystallized product is triturated at 80° C. for one hour on the rotavapor
  6. filtrationThe product is filtered off
  7. washwashed twice with water (200 mL each washing)
  8. customdried

出典と根拠

ORDレコード
ord-7a720cb3423b459b882767d5664d7c88
出典データセット
uspto-grants-2014_04
特許番号
US08710093B2

関連ノート

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