2-Aminothiazole → HCID 23118584, compound

HRID 1348835Notes

Reaction equation

HRID 1348835 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]([F:23])[CH:17]=1.C(N(CC)CC)C.[Cl:31]C(Cl)(O[C:35](=[O:41])OC(Cl)(Cl)Cl)Cl.[NH2:43][C:44]1[S:45][CH:46]=[CH:47][N:48]=1>C(Cl)(Cl)Cl.O>[ClH:31].[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:35]([NH:43][C:44]2[S:45][CH:46]=[CH:47][N:48]=2)=[O:41])=[C:18]([F:23])[CH:17]=1

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 94429TriphosgeneHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

Product 1

HCID 23118584HCID 23118584, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (12 g) was dissolved in chloroform (350 ml) and triethylamine (50 ml) to prepare a solution. A solution of triphosgene (12 g) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 30 min. Next, 2-aminothiazole (4.77 g) was added thereto, and the mixture was further stirred at room temperature overnight. Iced water was added to the reaction solution, and the mixture was extracted with chloroform. The organic layer was washed with water and saturated brine and was then dried over anhydrous magnesium sulfate. The dried organic layer was filtered and was then concentrated, and ether was added to the residue for crystallization, followed by collection of the resultant crystal by filtration. The crystal was further washed with methanol and was collected by filtration. A 10% hydrogen chloride-methanol solution was added to the collected crystal, and the solution was concentrated. The resultant crystal was washed with a mixed solution composed of ether and ethanol to give 11.5 g of the title compound.

Workup

  1. stirringthe mixture was further stirred at room temperature overnight
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialwas then dried over anhydrous magnesium sulfate
  5. filtrationThe dried organic layer was filtered
  6. concentrationwas then concentrated
  7. additionether was added to the residue for crystallization
  8. customfollowed by collection of the resultant crystal
  9. filtrationby filtration
  10. washThe crystal was further washed with methanol
  11. filtrationwas collected by filtration
  12. additionA 10% hydrogen chloride-methanol solution was added to the collected crystal
  13. concentrationthe solution was concentrated
  14. washThe resultant crystal was washed with a mixed solution

Sources & evidence

ORD record
ord-f0f0cec56d95412fb9627f0ffb5c4ee8
Source dataset
uspto-grants-2007_05
Patent number
US07211587B2

Reaction notes

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