Benzyl Chloride → 2-Benzyloxy-3,6-bis(2,5-dimethoxy-4-benzoylaminophenylaminocarbonyl)naphthalene

HRID 1957797Notes

Reaction equation

HRID 1957797 reaction equation
[OH:1][C:2]1[C:11]([C:12]([NH:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([NH:23][C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:17][C:16]=2[O:32][CH3:33])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:34]([NH:36][C:37]3[CH:42]=[C:41]([O:43][CH3:44])[C:40]([NH:45][C:46](=[O:53])[C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[CH:39][C:38]=3[O:54][CH3:55])=[O:35])[CH:8]=2)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:62](Cl)[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1>CN(C)C=O>[CH2:62]([O:1][C:2]1[C:11]([C:12]([NH:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([NH:23][C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:17][C:16]=2[O:32][CH3:33])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:34]([NH:36][C:37]3[CH:42]=[C:41]([O:43][CH3:44])[C:40]([NH:45][C:46](=[O:53])[C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[CH:39][C:38]=3[O:54][CH3:55])=[O:35])[CH:8]=2)[CH:3]=1)[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 211919812-Hydroxy-3,6-bis(2,5-dimethoxy-4-benzoylaminophenylaminocarbonyl)naphthalene

Product 1

HCID 211919802-Benzyloxy-3,6-bis(2,5-dimethoxy-4-benzoylaminophenylaminocarbonyl)naphthaleneYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-Hydroxy-3,6-bis(2,5-dimethoxy-4-benzoylaminophenylaminocarbonyl)naphthalene (2.5 g) obtained in Example 10 was mixed with N,N-dimethylformamide (30 g) and the mixture was dissolved by heating to 100° C. under a nitrogen atmosphere. To the solution, potassium carbonate (0.5 g) was gradually added and benzyl chloride (0.46 g) was added dropwise and the mixed solution was reacted for 5 hours. After the completion of the reaction, the reaction solution was cooled to room temperature, filtered and then washed with water and methanol to obtain 2.65 g of 2-benzyloxy-3,6-bis(2,5-dimethoxy-4-benzoylaminophenylaminocarbonyl)naphthalene as a greenish yellow crystal (DSC analysis value: 282.8° C.)

Workup

  1. dissolutionthe mixture was dissolved
  2. customthe mixed solution was reacted for 5 hours
  3. customAfter the completion of the reaction
  4. temperaturethe reaction solution was cooled to room temperature
  5. filtrationfiltered
  6. washwashed with water and methanol

Sources & evidence

ORD record
ord-66cc8d34e25a4fe4ab9f282551779b87
Source dataset
uspto-grants-1998_07
Patent number
US05786523

Reaction notes

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