Tetrahydrofuran → 6-chloro-3-methylspiro[1H-quinazoline-4,5'-imidazolidine]-2,2',4'-trione

HRID 34544

반응식

HRID 34544 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11](=[O:14])[NH:12][CH3:13])[C:6](=[O:15])[C:5]2=O.Br.C(S[C:21](=[NH:23])[NH2:22])C.C(N(CC)CC)C.[O:31]1CCCC1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]3([C:6](=[O:15])[NH:23][C:21](=[O:31])[NH:22]3)[N:12]([CH3:13])[C:11](=[O:14])[NH:7][C:8]2=[CH:9][CH:10]=1

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 200213S-Ethylisothiuronium bromideHCID 14229949HCID 14229949, 화합물

생성물 1

HCID 142299686-chloro-3-methylspiro[1H-quinazoline-4,5'-imidazolidine]-2,2',4'-trione수율 53.1%

실험 절차

5-Chloro-1-methylcarbamoylisatin (4.0 g) is dissolved in tetrahydrofuran (40 ml) and thereto are added 2-ethylisothiourea hydrobromide (4.0 g) and triethylamine (3.0 ml), and the mixture is stirred at room temperature for one hour. The reaction mixture is concentrated under reduced pressure to remove the solvent. To the residue [i.e. 6-chloro- 3-methyl-4-hydroxy-4-(2-ethylisothioureido)carbonyl-2-oxo-1,2,3,4-tetrahydroquinazoline] is added 10% hydrochloric acid (50 ml), and the mixture is stirred at 70°-80° C. for 3 hours. After cooling, the precipitates are taken by filtration to give 6-chloro-3-methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione (2.5 g, yield 53.1%).

후처리

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customto remove the solvent
  3. additionTo the residue [i.e. 6-chloro- 3-methyl-4-hydroxy-4-(2-ethylisothioureido)carbonyl-2-oxo-1,2,3,4-tetrahydroquinazoline] is added 10% hydrochloric acid (50 ml)
  4. stirringthe mixture is stirred at 70°-80° C. for 3 hours
  5. temperatureAfter cooling
  6. filtrationthe precipitates are taken by filtration

출처 및 근거

ORD 기록
ord-850eaaccdc6e40e698af6ee15b322d76
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04762839

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