Acetic Acid → N-[1-(Diphenylphosphoryl)butyl]urea

HRID 259210

反応式

HRID 259210 の反応式
[C:1]1([P:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:8]CC)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:17](=O)[CH2:18][CH2:19][CH3:20].[NH2:22][C:23]([NH2:25])=[O:24].C(O)(=O)C>ClC1C=CC=CC=1>[C:11]1([P:7](=[O:8])([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:17]([NH:22][C:23]([NH2:25])=[O:24])[CH2:18][CH2:19][CH3:20])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

6

反応物 4

HCID 176Acetic Acid2 回HCID 261ButanalHCID 1176Urea2 回HCID 69754Ethyl diphenylphosphinite

生成物 1

HCID 21423533N-[1-(Diphenylphosphoryl)butyl]urea

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

反応条件

温度
110 °C

実験手順

When a mixture of 0.50 mole of ethyl diphenylphosphinite 0.55 mole of n-butyraldehyde, and 0.25 mole of urea in 150 ml of chlorobenzene is warmed at 110° C. for 3 hr, there is only a slow reaction. The mixture is cooled to room temperature and 0.25 mole of acetic acid is added dropwise in ~10 minutes. The temperature increases to 65° during this addition; the urea dissolves and then a white solid product separates. The addition of another 0.25 mole of acetic acid causes no additional heat of reaction. The reaction mixture is warmed at 65°-80° for 9.5 hr and filtered, giving 44.4g. Recrystallization from ethylene glycol gives 26.5g of a white solid: mp 241°-244°; 31P nmr (CF3CO2H) -44.4 ppm; ms M+ = 316 (theory 316).

後処理

  1. customa slow reaction
  2. temperatureThe mixture is cooled to room temperature
  3. temperatureThe temperature increases to 65° during this addition
  4. temperatureno additional heat of reaction
  5. temperatureThe reaction mixture is warmed at 65°-80° for 9.5 hr
  6. filtrationfiltered
  7. customgiving 44.4g
  8. customRecrystallization from ethylene glycol

出典と根拠

ORDレコード
ord-62254713c68e457ca0aaece535293c8d
出典データセット
uspto-grants-1977_07
特許番号
US04036913

関連ノート

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