1,3,5-Trimethoxybenzene → HCID 11663517, compound

HRID 2057059Notes

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]=[C:32]([O:34][CH3:35])[CH:31]=[C:30]([O:36][CH3:37])[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:29]3[C:30]([O:36][CH3:37])=[CH:31][C:32]([O:34][CH3:35])=[CH:33][C:28]=3[O:27][CH3:26])[N:7]=2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of compound 133 (0.5 grams), 1,3,5-trimethoxybenzene (0.2 grams) and AlCl3 (0.2 grams) in dichloroethane (10 mL) was stirred under nitrogen atmosphere. It was then heated at 80° C. for 3 hours. The reaction mixture was poured into ice-cold water (50 mL), extracted with chloroform and the organic layer was washed with water followed by concentration. The residue thus obtained was purified by column chromatography using petroleum ether-ethyl acetate to afford the N-(3-Chloro-4-methoxy-phenyl)-N′-cycloheptyl-6-(2,4,6-trimethoxy-phenyl)-[1,3,5]triazine-2,4-diamine.

Workup

extractionextracted with chloroform
washthe organic layer was washed with water
concentrationfollowed by concentration
customThe residue thus obtained
customwas purified by column chromatography

Sources & evidence

ORD record: ord-368b807de5724e36ac37f5ffda02a533
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07335770B2

Reaction notes

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