Methyl Isocyanate → 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-2-(N-methylcarbamoyl)oxymethyl-1H-imidazole

HRID 1416011

반응식

HRID 1416011 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][OH:17])=[N:12][C:11]=2[CH:18]([CH3:20])[CH3:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:21][N:22]=[C:23]=[O:24].CCCC[Sn](O[Sn](CCCC)(CCCC)CCCC)(CCCC)CCCC>O1CCCC1>[Cl:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][O:17][C:23](=[O:24])[NH:22][CH3:21])=[N:12][C:11]=2[CH:18]([CH3:20])[CH3:19])[CH:3]=[C:2]([Cl:1])[CH:7]=1

참가 물질

5

반응물 3

HCID 12228Methyl IsocyanateHCID 473916(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)methanolHCID 16682746Bis(tributyltin) oxide

생성물 1

HCID 4739525-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-2-(N-methylcarbamoyl)oxymethyl-1H-imidazole수율 98%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In dry tetrahydrofuran (6 ml)was dissolved 0.300 g (0.91 mmol)of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methanol (Compound I-8)and 0.48 ml (8.15 mmol) of methylisocyanate. To this solution was added 0.04 ml of bis(tributyltin)oxide, and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was fractionated by silica gel chromatography (acetone:methylene chloride=1:4), and recrystallized from isopropyl ether to obtain 0.345 g of (Compound I-43)(yield 98%). mp 112-113° C.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customrecrystallized from isopropyl ether
  3. customto obtain 0.345 g of (Compound I-43)(yield 98%)

출처 및 근거

ORD 기록
ord-ea6b610e47d1439c882578b7ab3904b5
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05910506

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