4-Chlorobenzylamine → HCID 178429625、化合物

HRID 23622

反応式

HRID 23622 の反応式
[OH:1][C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[C:4]2[C:13]([CH3:18])=[C:14]([CH2:16][OH:17])[S:15][C:3]=12.[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>Cl>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:25][C:8]([C:7]2[C:2]([OH:1])=[C:3]3[S:15][C:14]([CH2:16][OH:17])=[C:13]([CH3:18])[C:4]3=[N:5][CH:6]=2)=[O:10])=[CH:22][CH:21]=1

参加物

4

反応物 2

HCID 660364-ChlorobenzylamineHCID 178469552HCID 178469552、化合物

生成物 1

HCID 178429625HCID 178429625、化合物収率 92.4%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
80 °C

実験手順

Ethyl 7-hydroxy-2-(hydroxymethyl)-3-methylthieno[3,2-b]pyridine-6-carboxylate (1.27 g, 4.77 mmol) was dissolved in 4-chlorobenzylamine (11.6 mL, 95.4 mmol) and heated to 80° C. for 18 hours. After cooling to room temperature, the mixture was treated with 1 N HCl (100 mL). After chilling in the refrigerator for 2 hrs, the resulting thick precipitate was collected and washed with copious amounts of 1 N HCl until all unreacted 4-chlorobenzylamine had been washed away. The resulting off-white solid was dried in vacuo to give the title compound (1.60 g). 1H NMR (DMSO-d6) δ 2.27 (3 H), 4.53 (2 H), 4.72 (2 H), 5.06 (1 H), 7.38 (4 H), 8.52 (1 H), 10.49 (1 H), 12.95 (1 H). HPLC retention time: 2.73 minutes; MS (ESI−) for C17H15ClN2O3S m/z 361, 363.

後処理

  1. temperatureAfter cooling to room temperature
  2. temperatureAfter chilling in the refrigerator for 2 hrs
  3. customthe resulting thick precipitate was collected
  4. washwashed with copious amounts of 1 N HCl until all unreacted 4-chlorobenzylamine
  5. washhad been washed away
  6. customThe resulting off-white solid was dried in vacuo

出典と根拠

ORDレコード
ord-82403aaca1324fadb28b6c6c0608259e
出典データセット
uspto-grants-2005_02
特許番号
US06852731B2

関連ノート

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