Phenyl isocyanate → n-(phenylcarbamoyl)glycine

HRID 703930Notes

Reaction equation

HRID 703930 reaction equation
Cl.C([O:4][C:5](=[O:8])[CH2:6][NH2:7])C.[C:9]1([N:15]=[C:16]=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>C1C=CC=CC=1>[C:9]1([NH:15][C:16]([NH:7][CH2:6][C:5]([OH:4])=[O:8])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 230718n-(phenylcarbamoyl)glycine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

7.0 g of glycine ethyl ester hydrochloride was suspended in 100 ml of benzene, and 10 ml of phenylisocyanate and 8 ml of triethylamine were added thereto. The mixture was stirred for 5 hours and benzene was distilled away. Ethyl acetate was added to the residue, washed with water and brine, and dried over anhydrous sodium sulfate. Ethyl acetate was distilled away and 100 ml of 1N aqueous solution of sodium hydroxide was added to the resulting residue. The solution was stirred at 50° C. for 2 hours. Insoluble substance was filtered off and the filtrate was acidified with concentrated hydrochloric acid. The precipitated crystals were collected by filtration and recrystallized from methanol/water to give 6.8 g of phenylcarbamoylglycine.

Workup

  1. distillationbenzene was distilled away
  2. additionEthyl acetate was added to the residue
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationEthyl acetate was distilled away
  6. addition100 ml of 1N aqueous solution of sodium hydroxide was added to the resulting residue
  7. stirringThe solution was stirred at 50° C. for 2 hours
  8. filtrationInsoluble substance was filtered off
  9. filtrationThe precipitated crystals were collected by filtration
  10. customrecrystallized from methanol/water

Sources & evidence

ORD record
ord-144f3996166242f8a6e9a9dfe42ad399
Source dataset
uspto-grants-1991_01
Patent number
US04985453

Reaction notes

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