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

HRID 1099060Notes

Reaction equation

HRID 1099060 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-742cc1f03c984f4b9e5378f740e972db
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

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