Hydrochloric Acid → HCID 86601210, compound

HRID 349255Notes

Reaction equation

HRID 349255 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.CCOC(C)=O.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

Dissolve the crude [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) and stir at RT. After 2 h., add the reaction mixture to EtOAc (150 mL) and 0.5 N HCl (200 mL), and separate the layers. Extract the aqueous layer with EtOAc (50 mL). Combine the organic layers and wash with saturated, aqueous sodium bicarbonate (100 mL) and 1.0 N HCl (100 mL). Dry the organic layer over MgSO4, 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, 5H), 5.86 (s, 2H); MS (m/e): 400 (M++1).

Workup

  1. additionadd N,N-diispropylethylamine (6.77 mL, 0.039 mol)
  2. customseparate the layers
  3. extractionExtract the aqueous layer with EtOAc (50 mL)
  4. washCombine the organic layers and wash with saturated, aqueous sodium bicarbonate (100 mL) and 1.0 N HCl (100 mL)
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-9c206d04468c466f9ac835a6976dcdd4
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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