Triethylamine → HCID 22637159, compound

HRID 2416042Notes

Reaction equation

HRID 2416042 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][CH:46]=[C:47]([CH3:49])[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][CH:46]=[C:47]([CH3:49])[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 741432-Amino-4-methylthiazoleHCID 94429TriphosgeneHCID 218905643-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]aniline

Product 1

HCID 22637159HCID 22637159, compoundYield 129.6%

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-4-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. Next, diethyl ether was 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 (78.3 mg, yield 68%).

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. additionNext, diethyl ether was 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-0d3b139e8d1645f79c31679d57b11c78
Source dataset
uspto-grants-2004_11
Patent number
US06821987B2

Reaction notes

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