Triethylamine → HCID 22637150, compound

HRID 1348855Notes

Reaction equation

HRID 1348855 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1)[NH2:5].C(N(CC)CC)C.ClC(Cl)(O[C:35](=[O:41])OC(Cl)(Cl)Cl)Cl.[NH2:43][C:44]1[S:45][C:46]([CH3:49])=[CH:47][N:48]=1>C(Cl)(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:35]([NH:43][C:44]2[S:45][C:46]([CH3:49])=[CH:47][N:48]=2)=[O:41])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 3517702-Amino-5-methylthiazoleHCID 218905643-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]aniline

Product 1

HCID 22637150HCID 22637150, compoundYield 134.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

3-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]aniline (84 mg) was dissolved in chloroform (2.5 ml) and triethylamine (0.25 ml) to prepare a solution. A solution of triphosgene (38 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 5 min. Next, 2-amino-5-methylthiazole (32 mg) was added thereto, and the mixture was further stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was subjected to separatory extraction with chloroform. The organic layer was concentrated and was evaporated to dryness. Diethyl ether was then added to the solid, and the solid was collected by filtration. Further, the collected solid was washed with methyl alcohol to give the title compound (81.5 mg, yield 70%).

Workup

  1. stirringthe mixture was further stirred at room temperature overnight
  2. extractionthe mixture was subjected to separatory extraction with chloroform
  3. concentrationThe organic layer was concentrated
  4. customwas evaporated to dryness
  5. additionDiethyl ether was then added to the solid
  6. filtrationthe solid was collected by filtration
  7. washFurther, the collected solid was washed with methyl alcohol

Sources & evidence

ORD record
ord-cc26f9e913ae4e4f9a889fe07b85d970
Source dataset
uspto-grants-2007_05
Patent number
US07211587B2

Reaction notes

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