Chloroacetonitrile → HCID 59547214, compound

HRID 1529831Notes

Reaction equation

HRID 1529831 reaction equation
[Se-2:1].[Na+].[Na+].Cl[C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8].Cl[CH2:14][C:15]#[N:16].C[O-].[Na+]>CN(C=O)C.CO.O>[NH2:8][C:7]1[C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[Se:1][C:14]=1[C:15]#[N:16]

Participants

8

Reactant 4

HCID 7856ChloroacetonitrileHCID 133912-ChlorobenzonitrileHCID 73973Sodium selenideHCID 10942334Sodium Methoxide

Product 1

HCID 59547214HCID 59547214, compoundYield 59.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
105 °C

Procedure

To a suspension of sodium selenide (9.14 g, 72.6 mmol) in DMF (72 mL) was added a solution of 2-chlorobenzonitrile (10 g, 72.6 mmol) in DMF (25 mL) at rt for 5 min and stirred the mixture at 100-110° C. for 24 h. Then chloroacetonitrile (5.48 mL, 72.6 mmol) was added dropwise to the reaction mixture and again stirred at 60-70° C. for 2 h. Then, a solution of sodium methoxide (3.9 g, 72.6 mmol) in dry methanol (24 mL) was added dropwise and stirring was continued for 2 h at the same temperature. The mixture was allowed to rt and poured into cold water and stirred for 30 min. The precipitated solid was filtered, washed with water and dried to give the product as an off-white color solid (9.5 g, 59%), mp 157-159° C.

Workup

  1. stirringagain stirred at 60-70° C. for 2 h
  2. stirringstirring
  3. waitwas continued for 2 h at the same temperature
  4. customwas allowed to rt
  5. stirringstirred for 30 min
  6. filtrationThe precipitated solid was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-7e2f8e9bb56749c8bcae77701e3c5f5b
Source dataset
uspto-grants-2015_07
Patent number
US09090633B2

Reaction notes

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