Toluene → HCID 58533508, compound

HRID 1627007Notes

Reaction equation

HRID 1627007 reaction equation
ClC(Cl)([O:4][C:5](=O)[O:6]C(Cl)(Cl)Cl)Cl.[Cl:13][C:14]1[CH:15]=[C:16]([C:21]2([C:34]([F:37])([F:36])[F:35])[O:25][N:24]=[C:23]([C:26]3[CH:27]=[CH:28][C:29]([Cl:33])=[C:30]([CH:32]=3)[NH2:31])[CH2:22]2)[CH:17]=[C:18]([Cl:20])[CH:19]=1.O1CCCC1.[C:43]1([CH3:49])[CH:48]=CC=C[CH:44]=1>>[Cl:33][C:29]1[CH:28]=[CH:27][C:26]([C:23]2[CH2:22][C:21]([C:16]3[CH:17]=[C:18]([Cl:20])[CH:19]=[C:14]([Cl:13])[CH:15]=3)([C:34]([F:36])([F:35])[F:37])[O:25][N:24]=2)=[CH:32][C:30]=1[NH:31][C:5](=[O:4])[O:6][C:43]([CH3:49])([CH3:48])[CH3:44]

Participants

5

Reactant 4

HCID 1140Toluene3×HCID 8028TetrahydrofuranHCID 94429TriphosgeneHCID 59355663HCID 59355663, compound

Product 1

HCID 58533508HCID 58533508, compound

Conditions

Temperature
80 °C

Procedure

Triphosgene (6.3 g) was dissolved in toluene (50 mL), and thereto was added dropwise a solution of 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-chloroaniline (8.7 g) obtained by Reference Production Example 20 in toluene (50 mL) and tetrahydrofuran (10 mL) at room temperature. To the reaction solution was added toluene (50 mL), and the mixture was stirred at 80° C. for 1 hour. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure, and thereto was added tert-butanol (100 mL). To this solution was added dropwise triethylamine (14.6 g) at room temperature, and the mixture was stirred at the same temperature for 16 hours. To the reaction mixture was added an aqueous saturated sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain tert-butyl {2-chloro-5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]phenyl}carbamate (9.81 g).

Workup

  1. customat room temperature
  2. temperatureAfter cooling to room temperature
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionwas added tert-butanol (100 mL)
  5. additionTo this solution was added dropwise triethylamine (14.6 g) at room temperature
  6. stirringthe mixture was stirred at the same temperature for 16 hours
  7. additionTo the reaction mixture was added an aqueous saturated sodium hydrogen carbonate solution
  8. extractionthe mixture was extracted with chloroform
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ba03a55e5fc941a7ac42eacff66b7ff0
Source dataset
uspto-grants-2014_07
Patent number
US08785485B2

Reaction notes

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