Pyridine → 2-Carbomethoxy-5-tert-butyl-3-furyl isocyanate

HRID 1698905ノート

反応式

HRID 1698905 の反応式
[C:1](Cl)([Cl:3])=[O:2].[NH2:5][C:6]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[O:8][C:7]=1[C:15]([O:17][CH3:18])=[O:16].[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[C:15]([C:7]1[O:8][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:6]=1[N:5]=[C:1]=[O:2])([O:17][CH3:18])=[O:16].[ClH:3].[NH+:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 6371PhosgeneHCID 18322376Methyl 3-amino-5-(tert-butyl)furan-2-carboxylate

生成物 2

HCID 183223842-Carbomethoxy-5-tert-butyl-3-furyl isocyanateHCID 21584435Pyridinium hydrochloride

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of phosgene (1.93M in toluene, 9.7 mL, 18.6 mmol, 3.0 equiv) in CH2Cl2 (80 mL) at 0° C. was added a solution of methyl 3-amino-5-tert-butylfuran-2-carboxylate (1.23 g, 6.2 mmol) and pyridine (1.97 g, 24.9 mmol, 4.0 equiv) in CH2Cl2 (20 mL). The reaction mixture was allowed to slowly warm to room temp. and rapidly form a precipitate. The resulting slurry was stirred at room temp. for 1 h, then concentrated under reduced pressure to give 2-carbomethoxy-5-tert-butyl-3-furyl isocyanate and pyridinium hydrochloride. 2-Carbomethoxy-5-tert-butyl-3-furyl isocyanate: 1H NMR (CDCl3) δ1.25 (s, 9H), 4.85 (s, 3H), 5.90 (s, 1H). The mixture was used in the next step without further purification.

後処理

  1. temperatureto slowly warm to room temp.
  2. customrapidly form a precipitate
  3. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-4027bf23515b4fe291fd6fa24193eaca
出典データセット
uspto-grants-2002_02
特許番号
US06344476B1

反応ノート

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