Ethyl Acetate → 4-(azidomethyl)-5-chloro-1,3-dimethyl-1H-pyrazole

HRID 530793Notes

Reaction equation

HRID 530793 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[CH2:9]O.C1C=CC(P([N:25]=[N+:26]=[N-:27])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1.CC(=O)OCC>C1(C)C=CC=CC=1>[N:25]([CH2:9][C:3]1[C:4]([CH3:8])=[N:5][N:6]([CH3:7])[C:2]=1[Cl:1])=[N+:26]=[N-:27]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 13673186(5-chloro-1,3-dimethyl-1H-pyrazol-4-yl)methanol

Product 1

HCID 613734544-(azidomethyl)-5-chloro-1,3-dimethyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of compound 2 (538 mg, 3.36 mmol) in toluene (10 mL) was added DPPA (1.1 mL, 5.04 mmol) and DBU (0.6 mL, 6.72 mmol) at 0° C. After stirring for 1 hr, the reaction mixture was warmed to room temperature and stirred for 24 hr. EA (20 mL) was added and the mixture was washed with water, brine, concentrated to give a yellow solid which was used without further purification. LCMS (ESI) m/z=186 (M+H)+.

Workup

  1. stirringstirred for 24 hr
  2. washthe mixture was washed with water, brine
  3. concentrationconcentrated
  4. customto give a yellow solid which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-bbdd22a442f946d58134a1e30e1dea0f
Source dataset
uspto-grants-2016_05
Patent number
US09353104B2

Reaction notes

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