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

HRID 1698905노트

반응식

HRID 1698905 반응식
[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

참가 물질

6

반응물 3

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

생성물 2

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-4027bf23515b4fe291fd6fa24193eaca
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06344476B1

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