Chloroacetonitrile → HCID 86646892, compound

HRID 1097230Notes

Reaction equation

HRID 1097230 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 81.3%

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, prepared from 0.75 g of selenium as described above) 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 stifling was continued for 1 h at the same temperature. The mixture was allowed to room temperature (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 (1.3 g, 81%), mp 208-210° C. 1H NMR (400 MHz, DMSO-d6): δ 8.68 (1H, d, J=4.4 Hz, H-6), 8.47 (1H, d, J=8.4 Hz, H-4), 7.55 (1H, dd, J=8.0, 4.8 Hz, H-5), 7.24 (2H, s, —NH2).

Workup

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

Sources & evidence

ORD record
ord-6a6c8fde7a79445db5228b56143c76f8
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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