Water → N-[(4-Fluoro-3-nitrophenyl)carbamoyl]glycine, ethyl ester

HRID 52411

반응식

HRID 52411 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].Cl.[CH2:15]([O:17][C:18](=[O:21])[CH2:19][NH2:20])[CH3:16].C(N(CC)CC)C.O>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:20][CH2:19][C:18]([O:17][CH2:15][CH3:16])=[O:21])=[O:10])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 1441174-Fluoro-3-nitrophenyl isocyanateHCID 2723640Glycine ethyl ester, hydrochloride

생성물 1

HCID 85708209N-[(4-Fluoro-3-nitrophenyl)carbamoyl]glycine, ethyl ester수율 56.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 4-fluoro-3-nitrophenyl isocyanate (10 g, 0.055 mol) in anhydrous tetrahydrofuran is cooled to 0° C., treated with glycine ethyl ester hydrochloride (7.7 g, 0.055 mol), treated with triethylamine (5.56 g, 0.055 mol) while maintaining the temperature below 10° C., stirred at room temperature for 1 hour and poured into water. The aqueous mixture is extracted with ether. The combined organic extracts are washed sequentially with 1N hydrochloric acid and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a solid which is air-dried to give the title product as a yellow solid (8.8 g, mp 115°-120° C.).

후처리

  1. temperaturewhile maintaining the temperature below 10° C.
  2. extractionThe aqueous mixture is extracted with ether
  3. washThe combined organic extracts are washed sequentially with 1N hydrochloric acid and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a solid which
  7. customis air-dried

출처 및 근거

ORD 기록
ord-0ced5012f76c486b8fdc49c48e1c0d68
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616706

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