Potassium Carbonate → HCID 86631471, compound

HRID 335090Notes

Reaction equation

HRID 335090 reaction equation
C([NH:9][C:10](=[S:32])[NH:11][C:12]1[C:17]([O:18][C:19]2[CH:20]=[C:21]([CH:27]=[CH:28][C:29]=2[Cl:30])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][C:15]([Br:31])=[CH:14][N:13]=1)(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C(O)C>[Br:31][C:15]1[CH:16]=[C:17]([O:18][C:19]2[CH:20]=[C:21]([CH:27]=[CH:28][C:29]=2[Cl:30])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:12]([NH:11][C:10]([NH2:9])=[S:32])=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86631470HCID 86631470, compound

Product 1

HCID 86631471HCID 86631471, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-(2-(3-benzoylthioureido)-5-bromopyridin-3-yloxy)-4-chlorobenzoate (8.05 g, 15.1 mmol) and K2CO3 (10.4 g, 75.3 mmol) were placed in ethanol (150 mL) and heated to reflux for 2 days and then cooled. The reaction mixture was filtered and the filtrate was concentrated, triturated with water, and dried. The remaining solid was dissolved in CH2Cl2 and purified by silica gel chromatography to give ethyl 3-(5-bromo-2-thioureidopyridin-3-yloxy)-4-chlorobenzoate (1.70 g, 26.2% yield).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 days
  3. temperaturecooled
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. customtriturated with water
  7. customdried
  8. dissolutionThe remaining solid was dissolved in CH2Cl2
  9. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-faba8d47198a4b57bbc23e5359f091f4
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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