Triethylamine → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-nitrophenyl}-N'-[2-(ethyl-3-methylanilino)ethyl]urea

HRID 721563Notes

Reaction equation

HRID 721563 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:22]=[CH:21][C:19]([NH2:20])=[C:18]([N+:23]([O-:25])=[O:24])[CH:17]=1.C(N(CC)CC)C.ClC(Cl)(O[C:37](=[O:43])OC(Cl)(Cl)Cl)Cl.[CH2:45]([N:47]([C:51]1[CH:56]=[CH:55][CH:54]=[C:53]([CH3:57])[CH:52]=1)[CH2:48][CH2:49][NH2:50])[CH3:46]>C(Cl)(Cl)Cl.O>[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:22]=[CH:21][C:19]([NH:20][C:37]([NH:50][CH2:49][CH2:48][N:47]([CH2:45][CH3:46])[C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([CH3:57])[CH:52]=2)=[O:43])=[C:18]([N+:23]([O-:25])=[O:24])[CH:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 879841,2-Ethanediamine, N1-ethyl-N1-(3-methylphenyl)-HCID 94429TriphosgeneHCID 218907304-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-nitroaniline

Product 1

HCID 21890764N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-nitrophenyl}-N'-[2-(ethyl-3-methylanilino)ethyl]ureaYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-nitroaniline (100 mg) was dissolved in chloroform (10 ml) and triethylamine (1 ml) to prepare a solution. A solution of triphosgene (131 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 10 min. Next, N1-ethyl-N1-(3-methylphenyl)-1,2-ethanediamine (78 mg) was added thereto, and the mixture was further stirred at room temperature for one hr. Water was added to stop the reaction, and the reaction solution was then extracted with chloroform, followed by concentration. The residue was purified on a column using chloroform/methanol to give the title compound (101 mg, yield 64%).

Workup

  1. stirringthe mixture was further stirred at room temperature for one hr
  2. customthe reaction
  3. extractionthe reaction solution was then extracted with chloroform
  4. concentrationfollowed by concentration
  5. customThe residue was purified on a column

Sources & evidence

ORD record
ord-fba1e5e55ac34f098ec241ec270dd092
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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