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Phenyl isocyanate → [(Anilinocarbonyl)amino]acetic acid

HRID 703930
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HRID 703930 반응식
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
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참가 물질

5

반응물 3

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

생성물 1

HCID 230718[(Anilinocarbonyl)amino]acetic acid

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-144f3996166242f8a6e9a9dfe42ad399
출처 데이터셋
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04985453

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