Diethyl Ether → 1-Hydroxy-1-(1-methylethyl)-3-(2,4,5-trimethylphenyl)urea

HRID 976636ノート

反応式

HRID 976636 の反応式
Cl.[CH:2]([NH:5][OH:6])([CH3:4])[CH3:3].C(OCC)C.[OH-].[Na+].[CH3:14][C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([CH3:22])=[CH:17][C:16]=1[N:23]=[C:24]=[O:25]>O>[OH:6][N:5]([CH:2]([CH3:4])[CH3:3])[C:24]([NH:23][C:16]1[CH:17]=[C:18]([CH3:22])[C:19]([CH3:21])=[CH:20][C:15]=1[CH3:14])=[O:25]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 170873N-Isopropylhydroxylamine HydrochlorideHCID 127935172,4,5-Trimethylphenyl isocyanate

生成物 1

HCID 199673751-Hydroxy-1-(1-methylethyl)-3-(2,4,5-trimethylphenyl)urea収率 67.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

A solution of N-isopropylhydroxylamine hydrochloride (1.85 g, 16.5 mmol) in water (5 mL) was combined with diethyl ether (50 mL) then cooled in an ice bath. A solution of sodium hydroxide (0.72 g, 18 mmol) in water (10 mL) was added over a 10 minute period. The reaction mixture was stirred for 10 minutes then 2,4,5-trimethylphenyl isocyanate (2.42 g, 15 mmol) was added as a solid. The reaction mixture was stirred at ambient temperature for 18 hours. A white solid was isolated by filtration then recrystallized from hexanes/ethyl acetate to provide 2.4 g of the desired product as a white crystalline solid, m.p. 176.2°-176.8° C. Analysis: Calculated for C13H20N2O2 : %C, 66.07; %H, 8.53; %N, 11.85; Found: %C, 65.85; %H, 8.35; %N, 11.68.

後処理

  1. temperaturethen cooled in an ice bath
  2. stirringThe reaction mixture was stirred at ambient temperature for 18 hours
  3. customA white solid was isolated by filtration
  4. customthen recrystallized from hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-f41654a6867848c88c9d135abf7b1948
出典データセット
uspto-grants-1997_03
特許番号
US05612377

反応ノート

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