Chloroacetonitrile → HCID 69910038, compound

HRID 2303469Notes

Reaction equation

HRID 2303469 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[OH:15])[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl[CH2:24][C:25]#[N:26]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:12])=[O:13])=[CH:7][C:6]=1[O:15][CH2:24][C:25]#[N:26])[CH3:2]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 69908919Ethyl 2-hydroxy-4-(methylsulfonyl)benzoate

Product 1

HCID 69910038HCID 69910038, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A stirring solution of 11 (6.0 g) in DMF (200 mL) was treated with K2CO3 (6 g) and chloroacetonitrile (6 mL) and heated at 75° C. overnight. The mixture was cooled and partitioned between 1:1 EtOAc/hexanes and H2O. The organic layer was washed with 1 M NaOH, washed with brine, dried (MgSO4), filtered, and evaporated. The residue was triturated with Et2O/hexanes. The resulting solid was collected by filtration giving 6.6 g of 2-cyanomethoxy-4-methanesulfonyl-benzoic acid ethyl ester 12.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between 1:1 EtOAc/hexanes and H2O
  3. washThe organic layer was washed with 1 M NaOH
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was triturated with Et2O/hexanes
  9. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-bf1baaea904c47a1bab9fabf6e29ef75
Source dataset
uspto-grants-2002_08
Patent number
US06433005B1

Reaction notes

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