Chlorosuccinimide → HCID 10844654, compound

HRID 2267410Notes

Reaction equation

HRID 2267410 reaction equation
[Cl:1]N1C(=O)CCC1=O.[S:9]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10]1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)(Cl)Cl.Cl(O)(=O)(=O)=O>[Cl:1][C:10]1[S:9][CH:13]=[CH:12][C:11]=1[CH2:14][C:15]#[N:16]

Participants

6

Reactant 3

HCID 31398ChlorosuccinimideHCID 837303-ThienylacetonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 10844654HCID 10844654, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 24247Perchloric AcidCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Perchloric acid (0.070 mL, 0.81 mmol) was added to a rapidly stirring suspension of N-chlorosuccinimide (10.8 g, 81.2 mmol) and 2-(thiophen-3-yl)acetonitrile (10.0 g, 81.2 mmol) in carbon tetrachloride (40 mL). After 3 h at room temperature, the reaction mixture was treated with solid NaHCO3 (300 mg, 3.6 mmol), then filtered and concentrated. The residue was purified by chromatography, eluting with a gradient of 5-15% EtOAc/hexanes to afford pure 2-(2-chlorothiophen-3-yl)acetonitrile as a pale yellow oil (4.23 g, 26.8 mmol, 33% yield). MS (M+H)+ 158/160.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography
  4. washeluting with a gradient of 5-15% EtOAc/hexanes

Sources & evidence

ORD record
ord-438ee1fae89d414cb5838a9a2b4c9280
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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