Phenyl chloroformate → (5-Cyclobutyl-2-methyl-2H-pyrazol-3-yl)-carbamic acid phenyl ester

HRID 1182109Notes

Reaction equation

HRID 1182109 reaction equation
[CH:1]1([C:5]2[CH:6]=[C:7]([NH2:11])[N:8]([CH3:10])[N:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:12]1([O:18][C:19](Cl)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O>[C:12]1([O:18][C:19](=[O:20])[NH:11][C:7]2[N:8]([CH3:10])[N:9]=[C:5]([CH:1]3[CH2:2][CH2:3][CH2:4]3)[CH:6]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 133248283-Cyclobutyl-1-methyl-1H-pyrazol-5-amine

Product 1

HCID 69361120(5-Cyclobutyl-2-methyl-2H-pyrazol-3-yl)-carbamic acid phenyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-Cyclobutyl-2-methyl-2H-pyrazol-3-ylamine (0.156 g, 1.03 mmol) in dimethylformamide (3 ml) cooled to 0° C., is treated with phenylchloroformate (0.13 ml, 1.03 mmol) dropwise and left to stir at 0° C. for 1 hour. The reaction mixture is partitioned between ethylacetate and 1.0 M hydrochloric acid solution, and the organic phase washed with water, dried over magnesium sulphate and evaporated to yield (5-Cyclobutyl-2-methyl-2H-pyrazol-3-yl)-carbamic acid phenyl ester. [M+H] 272.22

Workup

  1. waitleft
  2. customThe reaction mixture is partitioned between ethylacetate and 1.0 M hydrochloric acid solution
  3. washthe organic phase washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-7cd1c1c2f4fa405f9ecac626ed9e716f
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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