Chlorosuccinimide → HCID 178470414, compound

HRID 1941856Notes

Reaction equation

HRID 1941856 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]([CH:11]2[CH2:13][CH2:12]2)[CH:10]=1)=[O:5])[CH3:2].[Cl:14]N1C(=O)CCC1=O>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[NH:7][N:8]=[C:9]([CH:11]2[CH2:12][CH2:13]2)[C:10]=1[Cl:14])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178468609HCID 178468609, compound

Product 1

HCID 178470414HCID 178470414, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-cyclopropyl-2H-pyrazole-3-carboxylic acid ethyl ester (202 mg) in N,N-dimethylformamide (4 ml) was added at 0° C. N-chlorosuccinimide (199 mg) and stirring was continued at 22° C. for 15 hours. For the workup, The mixture was partitioned between water and ethyl acetate, the organic layer was dried, evaporated and the residue purified by chromatography on silica using a 8:1-mixture of n-heptane and ethyl acetate as the eluent to give 4-chloro-5-cyclopropyl-2H-pyrazole-3-carboxylic acid ethyl ester (215 mg) as a pale yellow liquid. MS (ISP): m/z=215.2 [M+H]+. b) To a solution of 4-chloro-5-cyclopropyl-2H-pyrazole-3-carboxylic acid ethyl ester (210 mg) in dioxane (4 ml) was added at 22° C. a solution of sodium hydroxide (3.0 M, 0.65 ml), and stirring was continued at 22° C. for 15 hours and at 60° C. for 3 hours. For the workup, the mixture was partitioned between aqueous hydrochloric acid (1.0 M) and ethyl acetate, the organic layer was dried and evaporated to give the title compound (161 mg) as a pale yellow solid. MS (ISP): m/z=184.8 [M−H]−.

Workup

  1. customFor the workup, The mixture was partitioned between water and ethyl acetate
  2. customthe organic layer was dried
  3. customevaporated
  4. customthe residue purified by chromatography on silica using a 8

Sources & evidence

ORD record
ord-49086176fc0049a988f9184ed0d072ae
Source dataset
uspto-grants-2013_03
Patent number
US08389513B2

Reaction notes

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