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

HRID 34544

反応式

HRID 34544 の反応式
[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

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 200213S-Ethylisothiuronium bromideHCID 14229949HCID 14229949、化合物

生成物 1

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

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-850eaaccdc6e40e698af6ee15b322d76
出典データセット
uspto-grants-1988_08
特許番号
US04762839

関連ノート

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