Hydrochloric Acid → HCID 86601210, compound

HRID 2251980Notes

Reaction equation

HRID 2251980 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([CH2:18][OH:19])[N:9]=[N:8]1.C(OCC)(=O)C.Cl>CS(C)=O>[F:28][C:2]([F:1])([F:27])[C:3]1[CH:4]=[C:5]([CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([CH:18]=[O:19])[N:9]=[N:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86601208HCID 86601208, compound

Product 1

HCID 86601210HCID 86601210, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Add sodium borohydride (1.70 g, 0.045 mol) to a solution of 1-(3,5-bis-trifluoromethylbenzyl)-5-phenyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester (5.0 g, 0.011 mol) in EtOH (70 mL). Heat to reflux and stir for 2 hours. Cool to room temperature. Add the reaction mixture to 0.5 N HCl (200 mL) and methylene chloride (200 mL). Separate layers and extract aqueous layer with methylene chloride (50 mL). Combine organic layers, dry (magnesium sulfate), filter and concentrate to give [1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-methanol. Dissolve [1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-methanol (3.90 g, 0.0097 mol) in DMSO (30 mL) and add N,N-diispropylethylamine (6.77 mL, 0.039 mol). To this solution add sulfur trioxide pyridine complex (3.09 g, 0.019 mol) in DMSO (30 mL). Stir for 2 hours. Add the reaction mixture to ethyl acetate (150 mL) and 0.5 N HCl (200 mL), and separate layers. Extract aqueous layer with ethyl acetate (50 mL). Combine organic layers and wash with saturated, aqueous sodium bicarbonate (100 mL) and 1.0 N HCl (100 mL). Dry organic layers (magnesium sulfate), filter and concentrate to give the title compound: 1H NMR (500 MHz, DMSO) δ 9.91 (s, 1H), 8.02 (s, 1H), 7.69 (s, 2H), 7.55-7.49 (m, 5 H), 5.86 (s, 2 H); Mass spectrum (m/e): 400 (M+1).

Workup

  1. customseparate layers
  2. washCombine organic layers and wash with saturated, aqueous sodium bicarbonate (100 mL) and 1.0 N HCl (100 mL)
  3. filtrationDry organic layers (magnesium sulfate), filter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-aecd5faba474480eb98a018576e64fee
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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