1,1'-Thiocarbonyldiimidazole → HCID 178486839, compound

HRID 1351188Notes

Reaction equation

HRID 1351188 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.[C:24](N1C=CN=C1)(N1C=CN=C1)=[S:25]>ClCCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([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:6][CH:7]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 21098409HCID 21098409, compound

Product 1

HCID 178486839HCID 178486839, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N4-(4-chloro-phenyl)-6,7-dimethoxy-quinazoline-4,5-diamine (120 mg, 0.36 mmol) (from Example 13, Step B, supra) in 1,2-dichloroethane (30 mL) was added 1,1′-thiocarbonyldiimidazole (0.65 g, 3.63 mmol) (Aldrich). 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 (1:3:0.05) as eluent to give the desired 3-(4-chloro-phenyl)-8,9-dimethoxy-1H,3H-1,3,4,6-tetraaza-phenalene-2-thione as a yellow solid. (Yield 110 mg, 82%).

Workup

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

Sources & evidence

ORD record
ord-b5e4bee05d3c467492820c7286f5d5e2
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

Loading…