2-Furanmethanethiol → HCID 10742479、化合物

HRID 248832

反応式

HRID 248832 の反応式
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[O:6][C:7]3[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=3[CH2:9][N:10]([C:11]([NH:13][CH2:14][C:15](=[O:18])[CH:16]=[CH2:17])=[O:12])[C:4]=2[CH:3]=1.[CH2:25]([SH:31])[C:26]1[O:30][CH:29]=[CH:28][CH:27]=1.N1CCCCC1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>C(Cl)Cl.CO.CCOC(C)=O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]2[O:6][C:7]3[CH:22]=[CH:21][CH:20]=[CH:19][C:8]=3[CH2:9][N:10]([C:11]([NH:13][CH2:14][C:15](=[O:18])[CH2:16][CH2:17][S:31][CH2:25][C:26]3[O:30][CH:29]=[CH:28][CH:27]=3)=[O:12])[C:4]=2[CH:3]=1

参加物

8

反応物 4

HCID 73632-FuranmethanethiolHCID 8082PiperidineHCID 66854Benzyltrimethylammonium hydroxideHCID 10831197HCID 10831197、化合物

生成物 1

HCID 10742479HCID 10742479、化合物

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 8-chloro-N-(2-oxo-3-butenyl)dibenz[b,f][1,4]oxazepin-10(11H)-carboxamide (0.75 gram), furfuryl mercaptan (0.23 mL), piperidine (0.069 mL), and N-benzyltrimethylammonium hydroxide (0.069 mL) in methylene chloride (12 mL) and methanol (3 mL) was stirred at room temperature for 6 hours. The reaction was diluted with methylene chloride (75 mL), washed with 75 mL each of 1N HCl (two times), water, saturated aqueous sodium bicarbonate, and brine, dried over MgSO4, and evaporated in vacuo. The crude product was purified by flash chromatography through silica gel 60 (350 mL) using 95:5 methylene chloride: ethyl acetate to yield a colorless oil. Analysis calculated for C23H21ClN2O4S×0.1 EtOAc: C, 60.34; H, 4.72; N, 6.01; Cl, 7.61; S, 6.88. Found: C, 59.94; H, 4.84; N, 5.87; Cl, 8.13; S, 6.65.

後処理

  1. washwashed with 75 mL each of 1N HCl (two times), water, saturated aqueous sodium bicarbonate, and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe crude product was purified by flash chromatography through silica gel 60 (350 mL)
  5. customethyl acetate to yield a colorless oil

出典と根拠

ORDレコード
ord-4f1d21f2d9974500b6b242551c69a2b2
出典データセット
uspto-grants-1993_05
特許番号
US05212169

関連ノート

読み込み中…