Hydrochloric Acid → HCID 86601208, compound

HRID 2251979Notes

Reaction equation

HRID 2251979 reaction equation
[BH4-].[Na+].C([O:5][C:6]([C:8]1[N:9]=[N:10][N:11]([CH2:19][C:20]2[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=2)[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O)C.Cl.C(Cl)Cl>CCO>[F:33][C:30]([F:31])([F:32])[C:22]1[CH:21]=[C:20]([CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=1)[CH2:19][N:11]1[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:8]([CH2:6][OH:5])[N:9]=[N:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 86601209HCID 86601209, compound

Product 1

HCID 86601208HCID 86601208, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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. temperatureHeat
  2. temperatureto reflux
  3. extractionSeparate layers and extract aqueous layer with methylene chloride (50 mL)
  4. dry with materialCombine organic layers, dry (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-1936449e049c4019816a3df6aedb27e1
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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