Carbon Dioxide → 1,3-Benzothiazol-6-ylacetonitrile

HRID 2245960Notes

Reaction equation

HRID 2245960 reaction equation
[C-:1]#[N:2].[K+].C(O)CO.O.C(=O)=O.[S:12]1[C:16]2[CH:17]=[C:18]([CH2:21]O)[CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1>O.CN(C=O)C>[S:12]1[C:16]2[CH:17]=[C:18]([CH2:21][C:1]#[N:2])[CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 9032Potassium CyanideHCID 178603856-(Hydroxymethyl)benzothiazoleHCID 20437942Ethylene glycol water

Product 1

HCID 592163101,3-Benzothiazol-6-ylacetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of potassium cyanide (0.68 g, 0.010 mol) in water (3.0 mL) was added under nitrogen to a cooled (with an ethylene glycol/water (4/1)/dry ice bath) solution of 1,3-benzothiazol-6-ylmethanol in DMF (30 mL). The reaction mixture was warmed to 0° C., and stirred for 30 min. Water was added and the reaction mixture was extracted with DCM. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was flash chromatographed on a silica gel column with ethyl acetate in hexane from 10-30% to afford the desired product (1.07 g). Analytical LCMS: (M+H)+=175.2.

Workup

  1. extractionthe reaction mixture was extracted with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed on a silica gel column with ethyl acetate in hexane from 10-30%

Sources & evidence

ORD record
ord-9378f7c786cf4ae598cfb53e2a6d9b33
Source dataset
uspto-grants-2010_03
Patent number
US07683060B2

Reaction notes

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