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

HRID 363166

반응식

HRID 363166 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 100° 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 100° 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-f1fe8bc5cbd84f3ca2ce9234f76f87e5
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05872253

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