Ethanolamine → 3-(2-Hydroxyethyl)-1H,3H-quinazoline-2,4-dione

HRID 1614606

반응식

HRID 1614606 반응식
C(O[C:4](=[O:17])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([O:14]CC)=O)C.[NH2:18][CH2:19][CH2:20][OH:21]>>[OH:21][CH2:20][CH2:19][N:18]1[C:4](=[O:17])[C:5]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:11][C:12]1=[O:14]

참가 물질

3

반응물 2

HCID 700EthanolamineHCID 41533612-[(Ethoxycarbonyl)amino]benzoic acid ethyl ester

생성물 1

HCID 710163-(2-Hydroxyethyl)-1H,3H-quinazoline-2,4-dione수율 71.3%

실험 절차

A mixture of 2-[(ethoxycarbonyl)amino]benzoic acid ethyl ester (65.75 g, 0.277 mol) and 2-aminoethanol (16.9 g, 0.277 mol) was refluxed for 2.5 days in 350 mL of xylenes. The reaction was cooled to room temperature and xylene was removed. Chloroform was added to the residue and a brown solid crystallized. The brown solid was filtered from the solution. The chloroform layer was extracted with water, dried (Na2SO4), filtered and the solvent was removed. The residue was placed in the freezer in isopropyl alcohol. The brown solid was triturated with isopropyl alcohol. Both produced a crystalline white solid which was dried in vacuo overnight at 80° C. This gave a total of 40.70 g (71.3% yield) of white crystalline solid, mp 250°-252° C.

후처리

  1. customxylene was removed
  2. additionChloroform was added to the residue
  3. customa brown solid crystallized
  4. filtrationThe brown solid was filtered from the solution
  5. extractionThe chloroform layer was extracted with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent was removed
  9. customThe brown solid was triturated with isopropyl alcohol
  10. customBoth produced a crystalline white solid which
  11. customwas dried in vacuo overnight at 80° C

출처 및 근거

ORD 기록
ord-30f4b6db320b4965a9d21d9c57362a3c
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05198449

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