Hydrochloric Acid → HCID 178516800, compound

HRID 84297Notes

Reaction equation

HRID 84297 reaction equation
C([O:4][C:5]1[CH:9]=[N:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)[N:6]=1)(=O)C.CO.[OH-].[Li+].Cl>O1CCOCC1.O>[Br:16][C:13]1[CH:12]=[CH:11][C:10]([N:7]2[N:6]=[C:5]([OH:4])[CH:9]=[N:8]2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 672483222-(4-bromophenyl)-2H-1,2,3-triazol-4-yl acetate

Product 1

HCID 178516800HCID 178516800, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(4-bromophenyl)-2H-1,2,3-triazol-4-yl acetate (520 mg, 1.84 mmol) was treated with methanol (10 ml) and water (10 ml) followed by 1,4-dioxane (5 ml). The resulting solution was treated with lithium hydroxide (265 mg, 11.1 mmol). The reaction mixture was stirred at RT for 36 hours. 1N HCl (40 ml) was added to the reaction mixture and the product was extracted with ethyl acetate (3×100 ml). The combined organic phases were dried over potassium carbonate, filtered, and concentrated. The crude material was purified by chromatography on silica gel (4:1 heptane:EtOAc 1:4 heptane:EtOAc) to furnish a light tan solid (440 mg, 98% TY). MS (LC/MS) m/z 240.21 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.33 (s, 1 H) 7.58 (d, J=8.98 Hz, 2 H) 7.78 (d, J=8.98 Hz, 2 H).

Workup

  1. extractionthe product was extracted with ethyl acetate (3×100 ml)
  2. dry with materialThe combined organic phases were dried over potassium carbonate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by chromatography on silica gel (4:1 heptane:EtOAc 1:4 heptane:EtOAc)
  6. customto furnish a light tan solid (440 mg, 98% TY)

Sources & evidence

ORD record
ord-2902f1628f114f5ab6e7c9871d194b69
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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