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

HRID 437531

반응식

HRID 437531 반응식
[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

참가 물질

6

반응물 4

HCID 176Acetic Acid2회HCID 261ButanalHCID 1176Urea2회HCID 69754Ethyl diphenylphosphinite

생성물 1

HCID 21423533N-[1-(Diphenylphosphoryl)butyl]urea수율 33.5%

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

반응 조건

온도
110 °C

실험 절차

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 addded 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).

후처리

  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

출처 및 근거

ORD 기록
ord-cfd1eb6a1ba74c039c92eb62da3219a4
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04031170

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