Chlorosuccinimide → ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylate

HRID 2274576Notes

Reaction equation

HRID 2274576 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[NH:8][N:7]=1)=[O:5])[CH3:2].[Cl:12]N1C(=O)CCC1=O>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:10]([Cl:12])=[C:9]([CH3:11])[NH:8][N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 77645Ethyl 5-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 604759ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester (4.45 g, 28.9 mmol) and N-chlorosuccinimide (5.01 g, 37.5 mmol) in dimethylformamide (60 mL) was stirred for 24 hours at ambient temperature. The reaction was then concentrated down and purified by eluting through a silica gel column with a 0 to 100% ethyl acetate/heptane gradient to afford the title compound (5.2 g, 96% yield) as a white solid. MS (ESI) [m/e, (M+H)+]=189.3. 1H NMR (400 MHz, chloroform-d) δ ppm 9.39 (br. s., 1H), 4.44 (q, J=7.1 Hz, 2H), 2.35 (s, 3H), 1.43 (t, J=7.1 Hz, 3H).

Workup

  1. concentrationThe reaction was then concentrated down
  2. custompurified
  3. washby eluting through a silica gel column with a 0 to 100% ethyl acetate/heptane gradient

Sources & evidence

ORD record
ord-a8dfb6982c9f460495835d74f2fe8681
Source dataset
uspto-grants-2015_09
Patent number
US09126980B2

Reaction notes

Loading…