Isatin → 3-Methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione

HRID 34548

反応式

HRID 34548 の反応式
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[CH3:12][N:13]=[C:14]=[O:15].C[NH:17][C:18]([N:20]1C2C(=CC=CC=2)C(=O)C1=O)=[O:19].Br.C(SC(=N)N)C>O1CCCC1.C(N(CC)CC)C>[CH3:12][N:13]1[C:4]2([C:2](=[O:3])[NH:20][C:18](=[O:19])[NH:17]2)[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:1][C:14]1=[O:15]

参加物

7

反応物 4

HCID 7054IsatinHCID 12228Methyl IsocyanateHCID 200213S-Ethylisothiuronium bromideHCID 2835543N-(methylcarbamoyl)isatin

生成物 1

HCID 142299883-Methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione収率 75%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒2 回

反応条件

温度
70 °C

実験手順

Isatin (294.3 g) is suspended in tetrahydrofuran (3 liter) and thereto are added with stirring triethylamine (279 ml) and methyl isocyanate (129.8 ml) at 15° C. The mixture is stirred at 20°-25° C. for 2.5 hours (1-methylcarbamoylisatin is produced in the mixture). To the reaction mixture are added 2-ethylisothiourea hydrobromide (444.2 g) and triethylamine (55.8 ml), and the mixture is refluxed for 2 hours. After cooling, the solvent is distilled off under reduced pressure. To the residue [i.e. 3-methyl-4-hydroxy-4-(2-ethylisothioureido)carbonyl-2-oxo1,2,3,4-tetrahydroquinazoline] is added 10% hydrochloric acid (4 liter) and the mixture is stirred at 70° C. for 4 hours. After cooling, the precipitates are taken by filtration, washed with water, methanol (1 liter) and chloroform (1 liter) in this order and then dried to give 3-methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione (369.2 g, yield 75 %).

後処理

  1. customis produced in the mixture)
  2. temperaturethe mixture is refluxed for 2 hours
  3. temperatureAfter cooling
  4. distillationthe solvent is distilled off under reduced pressure
  5. additionTo the residue [i.e. 3-methyl-4-hydroxy-4-(2-ethylisothioureido)carbonyl-2-oxo1,2,3,4-tetrahydroquinazoline] is added 10% hydrochloric acid (4 liter)
  6. temperatureAfter cooling
  7. filtrationthe precipitates are taken by filtration
  8. washwashed with water, methanol (1 liter) and chloroform (1 liter) in this order
  9. customdried

出典と根拠

ORDレコード
ord-5590a2d8fe894688ad10925b9cbadf48
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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