1-chloro-5-isocyanato-2,4-dimethoxybenzene → HCID 22132654, compound

HRID 1857256Notes

Reaction equation

HRID 1857256 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.[Cl:23][C:24]1[CH:25]=[C:26]([N:34]=[C:35]=[O:36])[C:27]([O:32][CH3:33])=[CH:28][C:29]=1[O:30][CH3:31]>C1(C)C=CC=CC=1>[Cl:23][C:24]1[CH:25]=[C:26]([NH:34][C:35]([NH:22][C:19]2[CH:18]=[CH:17][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:21][CH:20]=2)=[O:36])[C:27]([O:32][CH3:33])=[CH:28][C:29]=1[O:30][CH3:31]

Participants

4

Reactant 2

HCID 43898041-chloro-5-isocyanato-2,4-dimethoxybenzeneHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132654HCID 22132654, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (54 mg) was dissolved in toluene (5 ml) with heat, 3-chloro-4,6-dimethoxyphenyl isocyanate (76 mg) was added, and the admixture was refluxed with heat for 18 minutes. The reaction solution was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1) to obtain 93 mg of the title compound (yield: 100%)

Workup

  1. temperaturewith heat
  2. temperaturethe admixture was refluxed
  3. temperaturewith heat for 18 minutes
  4. customThe reaction solution was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record
ord-78f317a475ab49a0827e6181d9bb5507
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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