Hydrochloric Acid → 1-[2-(3-methylphenyl)-2H-tetrazol-5-yl]ethanone

HRID 2422727Notes

Reaction equation

HRID 2422727 reaction equation
C[Mg]Br.[CH2:4](N(CC)CC)C.[CH3:11][C:12]1[CH:13]=[C:14]([N:18]2[N:22]=[N:21][C:20]([C:23]([O:25]CC)=O)=[N:19]2)[CH:15]=[CH:16][CH:17]=1.Cl>C1(C)C=CC=CC=1.O>[CH3:11][C:12]1[CH:13]=[C:14]([N:18]2[N:22]=[N:21][C:20]([C:23](=[O:25])[CH3:4])=[N:19]2)[CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 25264098ethyl 2-m-tolyl-2H-tetrazole-5-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 252640991-[2-(3-methylphenyl)-2H-tetrazol-5-yl]ethanoneYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
-10 °C

Procedure

Methylmagnesium bromide (1070 mL, 1.50 mol, 1.4 M in tetrahydrofuran/toluene) in triethylamine (520 mL, 3.74 mol) was added via an addition funnel to a stirred solution of ethyl 2-(3-methylphenyl)-2H-tetrazole-5-carboxylate in dry toluene (1000 mL) at −10° C. for 5 hours. The mixture was continued to stir at −10° C. overnight. A cooled (+3° C.) solution of hydrochloric acid (37%, 500 mL) and water (500 mL) was added over 2 hours 20 minutes. The layers were separated and the organic layer was washed with water (500 mL) and brine (2×250 mL). The aqueous layer was extracted with toluene (3×500 mL) and the toluene was washed with brine (2×250 mL). The combined organic extracts were concentrated and purified on silica using dichloromethane as eluent. The concentrated product residue was triturated with petroleum ether, filtrated and dried under reduced pressure at room temperature to give the title product (90.86 g, 60%).

Workup

  1. additionwas added over 2 hours 20 minutes
  2. customThe layers were separated
  3. washthe organic layer was washed with water (500 mL) and brine (2×250 mL)
  4. extractionThe aqueous layer was extracted with toluene (3×500 mL)
  5. washthe toluene was washed with brine (2×250 mL)
  6. concentrationThe combined organic extracts were concentrated
  7. custompurified on silica
  8. customThe concentrated product residue was triturated with petroleum ether
  9. filtrationfiltrated
  10. customdried under reduced pressure at room temperature

Sources & evidence

ORD record
ord-7157c50a30df46abb3e7178b3cb58412
Source dataset
uspto-grants-2011_06
Patent number
US07960422B2

Reaction notes

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