1,3-Dimethoxybenzene → HCID 11656000, compound

HRID 2057058Notes

Reaction equation

HRID 2057058 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Cl:17])[CH:10]=2)[N:5]=[C:4]([NH:18][CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:3]=1.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClC(Cl)C>[Cl:17][C:11]1[CH:10]=[C:9]([NH:8][C:6]2[N:5]=[C:4]([NH:18][CH:19]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[N:3]=[C:2]([C:31]3[CH:32]=[CH:33][C:28]([O:27][CH3:26])=[CH:29][C:30]=3[O:34][CH3:35])[N:7]=2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

5

Reactant 3

HCID 90251,3-DimethoxybenzeneHCID 6451240Aluminum(III) ChlorideHCID 218970216-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

Product 1

HCID 11656000HCID 11656000, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of compound 133 (0.5 grams), 1,3-dimethoxybenzene (0.18 g) and AlCl3 (0.2 grams) in dichloroethane (10 mL) was stirred under nitrogen atmosphere at room temperature for 30 min. It was then heated at 80° C. for 3 hours with stirring. The reaction mixture was poured into ice-cold water (50 mL), extracted with chloroform (3×30 mL), dried over anhydrous Na2SO4 and concentrated under vacuum. The residue thus obtained was purified by column chromatography using petroleum ether-ethyl acetate to afford the expected product (yield 64%).

Workup

  1. temperatureIt was then heated at 80° C. for 3 hours
  2. stirringwith stirring
  3. extractionextracted with chloroform (3×30 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe residue thus obtained
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-2d9150f159e945eab6360e91966e47af
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

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