Phenyl Isothiocyanate → 1-Piperazinecarbothioamide, 4-(4-amino-6,7-dimethoxy-2-quinazolinyl)-N-phenyl-

HRID 364888Notes

Reaction equation

HRID 364888 reaction equation
[N:1]1([C:7]2[N:16]=[C:15]([NH2:17])[C:14]3[C:9](=[CH:10][C:11]([O:20][CH3:21])=[C:12]([O:18][CH3:19])[CH:13]=3)[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:22]1([N:28]=[C:29]=[S:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCOCC1>[C:22]1([NH:28][C:29]([N:4]2[CH2:5][CH2:6][N:1]([C:7]3[N:16]=[C:15]([NH2:17])[C:14]4[C:9](=[CH:10][C:11]([O:20][CH3:21])=[C:12]([O:18][CH3:19])[CH:13]=4)[N:8]=3)[CH2:2][CH2:3]2)=[S:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline

Product 1

HCID 30614491-Piperazinecarbothioamide, 4-(4-amino-6,7-dimethoxy-2-quinazolinyl)-N-phenyl-Yield 69.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

In 20 ml of dioxane, there was dissolved 0.87 g. (3 mmole) of 2-piperazino-4-amino-6,7-dimethoxyquinazoline. To the resultant solution was added dropwise a solution of 0.41 g. (3 mmole) of phenylisothiocyanate dissolved in 10 ml of dioxane at room temperature. The mixture was further stirred overnight. After evaporation of the solvent, the residue was chromatographed on silica gel and eluted with 20% dioxane-chloroform to obtain 0.89 g. of the desired product.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was chromatographed on silica gel
  3. washeluted with 20% dioxane-chloroform
  4. customto obtain 0.89 g

Sources & evidence

ORD record
ord-04adfef2fbde4940b6b617c27477a4cd
Source dataset
uspto-grants-1986_08
Patent number
US04607034

Reaction notes

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