1,1'-Thiocarbonyldiimidazole → HCID 178486838, compound

HRID 1351170Notes

Reaction equation

HRID 1351170 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:10]2[N:9]=[CH:8][N:7]=[C:6]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:5]=2[C:4]=1[NH2:22].[C:23](N1C=CN=C1)(N1C=CN=C1)=[S:24]>ClCCCl>[CH3:14][O:13][C:12]1[CH:11]=[C:10]2[C:5]3[C:6]([N:15]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:23](=[S:24])[NH:22][C:4]=3[C:3]=1[O:2][CH3:1])=[N:7][CH:8]=[N:9]2

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 21098395HCID 21098395, compound

Product 1

HCID 178486838HCID 178486838, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6,7-dimethoxy-N4-phenyl-quinazoline-4,5-diamine (80 mg, 0.27 mmol) (from Example 1, Step, C supra) in 1,2-dichloroethane (30 mL) was added 1,1′-thiocarbonyldiimidazole (0.58 g, 3.24 mmol) (Fluka). The reaction mixture was heated with stirring at 80° C. for 4 hours. The solvent was evaporated and the residue was purified by chromatography using EtOAc/CH2Cl2/Et3N (1:1:0.04) as eluent to give the desired 8,9-dimethoxy-3-phenyl-1H,3H-1,3,4,6-tetraaza-phenalene-2-thione as a gray solid. (Yield 50 mg (55%).

Workup

  1. temperatureThe reaction mixture was heated
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-af55aeaa77f1485ba2e1c5dd8f40f7ee
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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