Ethyl chloroformate → 2-[(Ethoxycarbonyl)amino]benzoic acid ethyl ester

HRID 1614605

反応式

HRID 1614605 の反応式
C(NC1C(=CC=CC=1)C(O)=O)C.[NH2:13][C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].Cl[C:26]([O:28][CH2:29][CH3:30])=[O:27]>>[CH2:19]([O:18][C:16](=[O:17])[C:15]1[CH:21]=[CH:22][CH:23]=[CH:24][C:14]=1[NH:13][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:20]

参加物

3

反応物 2

HCID 10928Ethyl chloroformateHCID 66695078HCID 66695078、化合物

生成物 1

HCID 41533612-[(Ethoxycarbonyl)amino]benzoic acid ethyl ester収率 97.6%

実験手順

A mixture of ethyl 2-aminobenzoate (ethyl anthranilate) (50.0 g, 0.30 mole) and ethyl chloroformate (32.8 g, 0.30 mole) in 400 mL of xylenes was heated at reflux for 8 hours. The xylene was removed and the residue was dissolved in chloroform. The chloroform layer was extracted with 5% sodium hydroxide, dried (Na2SO4), filtered, and the chloroform removed to give an oil which crystallized. The solid was triturated with isopropyl ether and placed in the freezer. Two crops of white solid were obtained and dried in vacuo overnight at room temperature. This provided 67.95 g (97.6% yield) of white crystalline solid, mp 41°-42° C.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 8 hours
  3. customThe xylene was removed
  4. dissolutionthe residue was dissolved in chloroform
  5. extractionThe chloroform layer was extracted with 5% sodium hydroxide
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe chloroform removed
  9. customto give an oil which
  10. customcrystallized
  11. customThe solid was triturated with isopropyl ether
  12. customTwo crops of white solid were obtained
  13. customdried in vacuo overnight at room temperature

出典と根拠

ORDレコード
ord-dce13410905a44db8cdf8713116dd4ce
出典データセット
uspto-grants-1993_03
特許番号
US05198449

関連ノート

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