1-Bromo-2-Chloroethane → 1-(1,3-Benzothiazol-6-yl)cyclopropanecarbonitrile

HRID 1099061Notes

Reaction equation

HRID 1099061 reaction equation
[OH-].[Na+].[S:3]1[C:7]2[CH:8]=[C:9]([CH2:12][C:13]#[N:14])[CH:10]=[CH:11][C:6]=2[N:5]=[CH:4]1.Br[CH2:16][CH2:17]Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[S:3]1[C:7]2[CH:8]=[C:9]([C:12]3([C:13]#[N:14])[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:6]=2[N:5]=[CH:4]1

Participants

6

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 592163101,3-Benzothiazol-6-ylacetonitrile

Product 1

HCID 592163041-(1,3-Benzothiazol-6-yl)cyclopropanecarbonitrileYield 24%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

50% aqueous sodium hydroxide (1.51 mL) was added to a mixture of 1,3-benzothiazol-6-ylacetonitrile (586 mg, 3.36 mmol), 1-bromo-2-chloroethane (335 mg, 4.04 mmol), benzyltriethylammonium chloride (76.6 mg, 3.36 mmol) at 50° C. The reaction mixture was stirred at 50° C. for 3 h. Water was added and the mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was flash chromatographed on a silica gel column with ethyl acetate in hexane from 0-30% to afford the desired product (157 mg, 24%). Analytical LCMS: (M+H)+=201.2.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed on a silica gel column with ethyl acetate in hexane from 0-30%

Sources & evidence

ORD record
ord-02236bcd507241ac89cf561117026bf8
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

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