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

HRID 363166

反応式

HRID 363166 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-f1fe8bc5cbd84f3ca2ce9234f76f87e5
出典データセット
uspto-grants-1999_02
特許番号
US05872253

関連ノート

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