Chlorosuccinimide → HCID 90030341, compound

HRID 1488149Notes

Reaction equation

HRID 1488149 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[N:17]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[N:16]=[CH:15][C:14]=2[CH3:26])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1C(=O)N([Cl:34])C(=O)C1>C(#N)C>[Cl:34][C:15]1[C:14]([CH3:26])=[C:13]([C:9]2[C:10]([CH3:12])=[CH:11][C:2]([CH3:1])=[C:3]([CH:8]=2)[C:4]([O:6][CH3:7])=[O:5])[N:17]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:23])[CH3:24])[N:16]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 90030064HCID 90030064, compound2×

Product 1

HCID 90030341HCID 90030341, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 2,4-dimethyl-5-(4-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)benzoate (compound 250.3, 3.0 g, 8.02 mmol) in acetonitrile (20 mL) was added NCS (1.07 g, 8.02 mmol). The mixture was stirred at room temperature overnight, then partitioned between EtOAc (200 mL) and water (50 mL). The organic layer was washed with saturated sodium thiosulfate (50 mL), brine (50 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was purified with by silica gel column chromatography (hexanes:EtOAc, 20:1) to yield the title compound as a colorless oil (2.0 g, 61%). m/z (ES+) 409 (M+H)+.

Workup

  1. custompartitioned between EtOAc (200 mL) and water (50 mL)
  2. washThe organic layer was washed with saturated sodium thiosulfate (50 mL), brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with by silica gel column chromatography (hexanes:EtOAc, 20:1)

Sources & evidence

ORD record
ord-570a93a8bcb848a68d1add02fa979618
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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