Acrylonitrile → HCID 57839027, compound

HRID 732948Notes

Reaction equation

HRID 732948 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[C:4]([C:6](=[CH:9]N(C)C)[C:7]#[N:8])=O.C(#N)C=C.Cl.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([O:34][CH3:35])[CH:33]=1)[C:28]([NH2:30])=[NH:29].C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[C:4]1[C:6]([C:7]#[N:8])=[CH:9][N:30]=[C:28]([C:27]2[CH:31]=[C:32]([O:34][CH3:35])[CH:33]=[C:25]([O:24][CH3:23])[CH:26]=2)[N:29]=1

Participants

6

Reactant 4

HCID 7855AcrylonitrileHCID 10942334Sodium Methoxide2×HCID 123012433,5-Dimethoxy-benzamidine HClHCID 533953932-(2,4-Dichlorobenzoyl)-3-(dimethylamino)prop-2-enenitrile

Product 1

HCID 57839027HCID 57839027, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of Step 2 acrylonitrile (1.5 g, 5.6 mmol) and 3,5-dimethoxybenzamidine hydrochloride (1.2 g, 5.6 mmol) in MeOH (30 mL) was added NaOMe (25% in MeOH, 2.56 mL, 11.2 mmol). The reaction was heated to reflux for 5 hr. Additional NaOMe (25% in MeOH, 2.56 mL, 11.2 mmol) was added and was kept for 16 hr. The reaction was cooled to ambient temperature and quenched by addition of H2O (50 mL). The reaction was filtered and the solid was washed with MeOH (40 mL) to give 4-(2,4-dichlorophenyl)-2-(3,5-dimethoxyphenyl)pyrimidine-5-carbonitrile (960 mg, 38.4%) as a white solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 5 hr
  3. customquenched by addition of H2O (50 mL)
  4. filtrationThe reaction was filtered
  5. washthe solid was washed with MeOH (40 mL)

Sources & evidence

ORD record
ord-f10b3ffa47a0438db377645a30483120
Source dataset
uspto-grants-2009_09
Patent number
US07589088B2

Reaction notes

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