1,1'-Thiocarbonyldiimidazole → HCID 178486837, compound

HRID 1351179Notes

Reaction equation

HRID 1351179 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:17]([NH2:19])=[C:16]([O:20][CH3:21])[C:15]([O:22][CH3:23])=[CH:14][C:13]=3[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:24](N1C=CN=C1)(N1C=CN=C1)=[S:25]>ClCCCl>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:9]3[C:18]4[C:13]([N:12]=[CH:11][N:10]=3)=[CH:14][C:15]([O:22][CH3:23])=[C:16]([O:20][CH3:21])[C:17]=4[NH:19][C:24]2=[S:25])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 21098407HCID 21098407, compound

Product 1

HCID 178486837HCID 178486837, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N4-(3-bromo-phenyl)-6,7-dimethoxy-quinazoline-4,5-diamine (80 mg, 0.21 mmol) (from Example 6, Step B, supra) in 1,2-dichloroethane (50 mL) was added 1,1′-thiocarbonyldiimidazole (0.38 g, 2.13 mmol) (Fluka). The reaction mixture was heated with stirring at 90° C. for 4 hours. The solvents were evaporated and the residue was purified by chromatography using EtOAc/CH2Cl2/Et3N (1:2:0.05) as eluent to give the desired 3-(3-bromo-phenyl)-8,9-dimethoxy-1H,3H-1,3,4,6-tetraaza-phenalene-2-thione as a yellow solid. (Yield 80 mg, 91%).

Workup

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

Sources & evidence

ORD record
ord-07f2d659daab466e8ddd3f5a6d1b398b
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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