Chlorosuccinimide → HCID 57826514, compound

HRID 2392223Notes

Reaction equation

HRID 2392223 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([OH:15])=[O:14])[S:5][C:6]=1[C:7]1[N:11]([CH3:12])[N:10]=[CH:9][CH:8]=1.[Cl:16]N1C(=O)CCC1=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([OH:15])=[O:14])[S:5][C:6]=1[C:7]1[N:11]([CH3:12])[N:10]=[CH:9][C:8]=1[Cl:16]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 57826829HCID 57826829, compound

Product 1

HCID 57826514HCID 57826514, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic acid (121 mg, 0.5 mmol) and N-chlorosuccinimide (67 mg, 0.5 mmol) in THF (5 mL) was stirred in a sealed tube at 70° C. After 4 hrs, the solution was concentrated and partitioned between DCM and H2O. The aqueous layer was extracted several times with DCM. The organic fractions were combined, concentrated and azeotropically dried with toluene to give the title compound as a brown oil (136 mg, 98%): LC-MS (ES) m/z=278 (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. custompartitioned between DCM and H2O
  3. extractionThe aqueous layer was extracted several times with DCM
  4. concentrationconcentrated
  5. dry with materialazeotropically dried with toluene

Sources & evidence

ORD record
ord-01977cb9a7c64d2facab2a5c54fdc4d0
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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