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

HRID 1489861Notes

Reaction equation

HRID 1489861 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 85708209N-[(4-Fluoro-3-nitrophenyl)carbamoyl]glycine, ethyl esterYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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, 0.052 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.).

Workup

  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. customdried over anhydrous
  5. concentrationmagnesium sulfate, and concentrated in vacuo
  6. customto obtain a solid which
  7. customis air-dried

Sources & evidence

ORD record
ord-6b290b5f62204fbab659e81e64159af2
Source dataset
uspto-grants-1997_10
Patent number
US05679791

Reaction notes

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