Ethanol → HCID 86728491, compound

HRID 2277772Notes

Reaction equation

HRID 2277772 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16]C(=O)C)[C:11]=1[F:20])[C:6](=O)[CH3:7])[CH3:2].F[C:23](F)(F)[CH2:24][OH:25].[CH3:28][S:29]([OH:32])(=[O:31])=[O:30].[CH2:33](O)[CH3:34]>CC(O)C.O>[CH3:28][S:29]([OH:32])(=[O:31])=[O:30].[F:20][C:11]1[C:12]([NH2:16])=[N:13][CH:14]=[CH:15][C:10]=1[CH2:9][C:5]1[C:4](=[O:21])[O:3][C:1]2[CH:2]=[C:24]([OH:25])[CH:23]=[CH:34][C:33]=2[C:6]=1[CH3:7]

Participants

7

Reactant 4

HCID 702EthanolHCID 6395Methanesulfonic AcidHCID 64092,2,2-TrifluoroethanolHCID 86728492HCID 86728492, compound

Product 1

HCID 86728491HCID 86728491, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

Under a nitrogen atmosphere, the oily product of step 3 (15.0 g) was dissolved in 2,2,2-trifluoroethanol (33 mL) Resorcinol (5.3 g, 47.9 mmol) and methanesulfonic acid (11.7 mL, 181 mmol) were added thereto at 24° C., and the mixture was stirred at 90° C. for 4 hours. The mixture was cooled to room temperature and allowed to stand for 13 hours, ethanol (33 mL) and water (11 mL) were then added, and the mixture was stirred at 90° C. for 4.5 hours. It was cooled to 55° C., 2-propanol (105 mL) was added, and the mixture was cooled to room temperature and allowed to stand for 14 hours. The precipitated crystals were collected by filtration, washed twice with 2-propanol (33 mL), and dried under reduced pressure to obtain the title compound (8.2 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. waitto stand for 13 hours
  3. stirringthe mixture was stirred at 90° C. for 4.5 hours
  4. temperatureIt was cooled to 55° C.
  5. temperaturethe mixture was cooled to room temperature
  6. waitto stand for 14 hours
  7. filtrationThe precipitated crystals were collected by filtration
  8. washwashed twice with 2-propanol (33 mL)
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-fe73712046ea48e8b003bffbb8a57caf
Source dataset
uspto-grants-2015_09
Patent number
US09133174B2

Reaction notes

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