Chloroacetonitrile → 3-Amino-5-phenylselenophene-2-carbonitrile

HRID 1097220Notes

Reaction equation

HRID 1097220 reaction equation
[Se-2:1].[Na+].[Na+].Cl[C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[CH:6][C:7]#[N:8].Cl[CH2:16][C:17]#[N:18].C[O-].[Na+]>CN(C=O)C.CO.O>[NH2:8][C:7]1[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[Se:1][C:16]=1[C:17]#[N:18]

Participants

8

Reactant 4

HCID 7856ChloroacetonitrileHCID 73973Sodium selenideHCID 27775113-Chloro-3-phenyl-2-propenenitrileHCID 10942334Sodium Methoxide

Product 1

HCID 866468883-Amino-5-phenylselenophene-2-carbonitrileYield 53%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
65 °C

Procedure

To a suspension of sodium selenide (4.62 g, 36.7 mmol, prepared from 2.9 g of selenium as described above) in DMF (37 mL) was added a solution of 3-chloro-3-phenylprop-2-enenitrile (6.0 g, 36.7 mmol) in DMF (14 mL) at rt for 5 min and stirred the mixture at 60-70° C. for 2 h. Then chloroacetonitrile (2.32 mL, 36.7 mmol) was added dropwise to the reaction mixture and again stirred at 60-70° C. for 2 h. Then, a solution of sodium methoxide (2.0 g, 36.7 mmol) in dry methanol (23 mL) was added dropwise and stirring 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 and washed with water. The solid was recrystallized from chloroform-hexane to give the product as a brown color solid (4.8 g, 53%), mp 162-164° C. (decomp). 1H NMR (400 MHz, CDCl3): δ 7.46-7.49 (2H, m, Ar—H), 7.37-7.39 (3H, m, Ar—H), 7.01 (1H, s, H-4), 4.55 (2H, br s, —NH2).

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 room temperature
  5. custom(rt)
  6. stirringstirred for 15 min
  7. filtrationThe precipitated solid was filtered
  8. washwashed with water
  9. customThe solid was recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-abb2273e242c434898075d73e51d5a62
Source dataset
uspto-grants-2012_03
Patent number
US08143237B2

Reaction notes

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