Triethylamine → 6,7-Dichloro-3-methyl-4-hydroxy-4-thioureidocarbonyl-2-oxo-1,2,3,4-tetrahydroquinazoline

HRID 34545Notes

Reaction equation

HRID 34545 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[N:7]([C:12](=[O:15])[NH:13][CH3:14])[C:6](=[O:16])[C:5]2=[O:17].[NH2:18][C:19]([NH2:21])=[S:20].C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:12](=[O:15])[N:13]([CH3:14])[C:5]2([OH:17])[C:6]([NH:18][C:19]([NH2:21])=[S:20])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723790ThioureaHCID 142299555,6-Dichloro-1-methylcarbamoylisatin

Product 1

HCID 142299966,7-Dichloro-3-methyl-4-hydroxy-4-thioureidocarbonyl-2-oxo-1,2,3,4-tetrahydroquinazolineYield 33.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5,6-Dichloro-1-methylcarbamoylisatin (9.6 g) is suspended in tetrahydrofuran (100 ml) and thereto are added thiourea (3.0 g) and triethylamine (5.6 ml), and the mixture is stirred at room temperature for 5 hours. The resulting precipitates are taken by filtration to give 6,7-dichloro-3-methyl-4-hydroxy-4-thioureidocarbonyl-2-oxo-1,2,3,4-tetrahydroquinazoline (4.1 g). M.p. 225-228° C.

Workup

  1. customThe resulting precipitates
  2. filtrationare taken by filtration

Sources & evidence

ORD record
ord-bcc70a3b9eb942c1b7c9a6cc28b10ae7
Source dataset
uspto-grants-1988_08
Patent number
US04762839

Reaction notes

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