Sodium Bicarbonate → HCID 18954849, compound

HRID 2380666Notes

Reaction equation

HRID 2380666 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[CH2:13][N:12]([C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[O:23])[N:11]=2)=[CH:6][CH:5]=1.C(=O)(O)[O-].[Na+]>COCCOC.[Ti](Cl)(Cl)(Cl)Cl>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH:14]([C:15]3[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=3)[CH2:13][N:12]([C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:34])[F:33])=[CH:27][CH:26]=3)=[O:23])[NH:11]2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 15405400HCID 15405400, compound

Product 1

HCID 18954849HCID 18954849, compoundYield 24.3%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 0.473 g (0.0025 mol) of titanium tetrachloride in 10 mL of 1,2-dimethoxyethane was added 0.189 g (0.0048 mol) of sodium borohydride all at once at 0° C. The green solution was stirred at 0° C. for 5 minutes and 0.500 g (0.0012 mol) of 3,4-bis(4-chlorophenyl)-4,5-dihydro-N-[4-(trifluoromethyl)phenyl]-1H-pyrazole-1-carboxamide dissolved in 5 mL of 1,2-dimethoxyethane was added dropwise over 5 minutes. The cooling bath was removed and the dark brown solution was stirred at room temperature for 3 hours. The crude reaction mixture was poured into 100 mL of saturated sodium bicarbonate solution and extracted with ethyl acetate (3×50 mL). The ethyl acetate was washed with brine (100 mL), dried over anhydrous magnesium sulfate, filtered and the solvent was removed under reduced pressure to afford a yellow solid. The crude reaction product was chromatographed on silica gel with ethyl acetate/hexanes (40%:60%) as eluent and afforded 0.140 g of the title compound as a white solid; mp 242°-243° C.

Workup

  1. additionwas added dropwise over 5 minutes
  2. customThe cooling bath was removed
  3. stirringthe dark brown solution was stirred at room temperature for 3 hours
  4. customThe crude reaction mixture
  5. extractionextracted with ethyl acetate (3×50 mL)
  6. washThe ethyl acetate was washed with brine (100 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure
  10. customto afford a yellow solid
  11. customThe crude reaction product
  12. customwas chromatographed on silica gel with ethyl acetate/hexanes (40%:60%) as eluent

Sources & evidence

ORD record
ord-2211801073dc48c4ab6178312e34cc5e
Source dataset
uspto-grants-1994_11
Patent number
US05369121

Reaction notes

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