Chloroacetonitrile → HCID 86646892, compound

HRID 1529832Notes

Reaction equation

HRID 1529832 reaction equation
[Se-2:1].[Na+].[Na+].Cl[C:5]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[CH:7][N:6]=1.Cl[CH2:14][C:15]#[N:16].C[O-].[Na+]>CN(C=O)C.CO.O>[NH2:12][C:11]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[Se:1][C:14]=1[C:15]#[N:16]

Participants

8

Reactant 4

HCID 7856ChloroacetonitrileHCID 73973Sodium selenideHCID 810792-ChloronicotinonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 86646892HCID 86646892, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
65 °C

Procedure

To a suspension of sodium selenide (0.9 g, 7.2 mmol) in DMF (7 mL) was added a solution of 2-chloropyridine-3-carbonitrile (1 g, 7.2 mmol) in DMF (3 mL) at rt for 5 min and stirred the mixture at 60-70° C. for 2 h. Then chloroacetonitrile (0.46 mL, 7.22 mmol) was added dropwise to the reaction mixture and again stirred at 60-70° C. for 2 h. Then, a solution of sodium methoxide (0.39 g, 7.2 mmol) in methanol (7 mL) was added dropwise and stirring was continued for 1 h at the same temperature. The mixture was allowed to rt and poured into cold water and stirred for 15 min. The precipitated solid was filtered, washed with water and dried to give the product as a yellow color solid (1.2 g, 75%), mp 208-210° C.

Workup

  1. stirringagain stirred at 60-70° C. for 2 h
  2. stirringstirring
  3. waitwas continued for 1 h at the same temperature
  4. customwas allowed to rt
  5. stirringstirred for 15 min
  6. filtrationThe precipitated solid was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-f6d49afc9d8c4258bc7e6744c4889a0d
Source dataset
uspto-grants-2015_07
Patent number
US09090633B2

Reaction notes

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