Tetrahydrofuran → HCID 178477272, compound

HRID 533668Notes

Reaction equation

HRID 533668 reaction equation
[NH2:1][C:2]1[C:3]([OH:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C1COCC1.Cl.[CH2:19]([S:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](O)=[O:25])[CH3:20].C(=O)([O-])O.[Na+]>O>[CH2:19]([S:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([NH:1][C:2]1[C:3]([OH:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1)=[O:25])[CH3:20]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 23157873-Amino-5-(trifluoromethyl)-1,2-dihydropyridin-2-oneHCID 679812702-Ethylsulfanylbenzoic acid hydrochloride

Product 1

HCID 178477272HCID 178477272, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-amino-5-trifluoromethylpyridin-2-ol (0.75 g) and THF (5 ml), 2-ethylsulfanylbenzoic acid hydrochloride (0.93 g) was added under ice-cooling, heated to room temperature, and stirred for 2 hours. After the mixture was allowed to stand overnight, the mixture was heated to 50° C., and stirred with heating for 6 hours. To the mixture, sodium hydrogen carbonate (0.35 g) was added, and stirred with heating for further 2.5 hours. After the mixture was allowed to stand, water was poured thereinto, and the precipitated solid was collected by filtration. The obtained solid was washed with water, and dried to give 1.37 g of 2-ethylsulfanyl-N-(2-hydroxy-5-trifluoromethylpyridin-3-yl)-benzamide (Compound (1B)-506).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. waitto stand overnight
  4. temperaturethe mixture was heated to 50° C.
  5. stirringstirred
  6. temperaturewith heating for 6 hours
  7. stirringstirred
  8. temperaturewith heating for further 2.5 hours
  9. filtrationthe precipitated solid was collected by filtration
  10. washThe obtained solid was washed with water
  11. customdried

Sources & evidence

ORD record
ord-749b48b601664bd183c36e0ad08f3ea7
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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