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

HRID 1416011

反応式

HRID 1416011 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-ea6b610e47d1439c882578b7ab3904b5
出典データセット
uspto-grants-1999_06
特許番号
US05910506

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