Terephthalic Acid → N,N'-bis(4-dimethylamino-2-methylquinolin-6-yl)-terephthalamide

HRID 890249Notes

Reaction equation

HRID 890249 reaction equation
[Cl-].COC1N=C(OC)N=C([N+:12]2([CH3:18])[CH2:17][CH2:16]OC[CH2:13]2)N=1.[C:19]([OH:30])(=O)[C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=1.[CH3:31][N:32]([CH3:45])[C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([NH2:43])[CH:41]=2)[N:36]=[C:35]([CH3:44])[CH:34]=1>CN(C)C=O.C(#N)C.C(OC(C)C)(C)C>[CH3:18][N:12]([CH3:13])[C:17]1[C:16]2[C:37](=[CH:38][CH:39]=[C:40]([NH:43][C:24](=[O:26])[C:23]3[CH:22]=[CH:21][C:20]([C:19]([NH:43][C:40]4[CH:41]=[C:42]5[C:37](=[CH:38][CH:39]=4)[N:36]=[C:35]([CH3:44])[CH:34]=[C:33]5[N:32]([CH3:45])[CH3:31])=[O:30])=[CH:28][CH:27]=3)[CH:41]=2)[N:36]=[C:35]([CH3:44])[CH:34]=1

Participants

7

Reactant 3

HCID 7489Terephthalic AcidHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 179088824-Dimethylamino-6-aminoquinaldine

Product 1

HCID 12052464N,N'-bis(4-dimethylamino-2-methylquinolin-6-yl)-terephthalamideYield 99.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

4-(4,6-Dimethoxy-1,3,5-triazine-2-yl)-4-methylmorpholinium chloride (177 mg) is added to a solution of 48 mg (0.29 mmol) of terephthalic acid and 128 mg (0.64 mmol) of 4-dimethylamino-6-aminoquinaldine in 6 mL of dimethylformamide, at a temperature in the region of 20° C. The mixture obtained is stirred at a temperature in the region of 20° C. for about 12 hours. The reaction mixture is successively taken up in 2 mL of acetonitrile and 2 mL of diisopropyl ether, and the precipitate thus obtained is slowly filtered on a 6 mL BOND-ELUT cartridge filled with sintered material. The insoluble matter obtained is washed with diisopropyl ether and then dried under argon. 154 mg of N,N′-bis(4-dimethylamino-2-methylquinolin-6-yl)-terephthalamide are thus obtained in the form of a beige powder of whose characteristics are the following:

Workup

  1. customThe mixture obtained
  2. filtrationis slowly filtered on a 6 mL BOND-ELUT cartridge
  3. additionfilled with sintered material
  4. customThe insoluble matter obtained
  5. washis washed with diisopropyl ether
  6. customdried under argon

Sources & evidence

ORD record
ord-860eb2daabb54d0aa8d3495620a4260b
Source dataset
uspto-grants-2006_02
Patent number
US06995175B2

Reaction notes

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