4-Amidinobenzamide Hydrochloride → 4-[5-(4-Cyanophenyl)-2-pyrimidinyl]benzamide

HRID 375506Notes

Reaction equation

HRID 375506 reaction equation
[Na].Cl.[C:3]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][CH:7]=1)(=[NH:5])[NH2:4].[C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23](=[CH:26]OC)[CH:24]=O)=[CH:19][CH:18]=1)#[N:16]>CO>[C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]=[N:5][C:3]([C:6]3[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][CH:7]=3)=[N:4][CH:26]=2)=[CH:19][CH:18]=1)#[N:16]

Participants

5

Reactant 3

HCID 27242934-Amidinobenzamide HydrochlorideHCID 5360545SodiumHCID 541002652-(4-Cyanophenyl)-3-methoxyacrolein

Product 1

HCID 189919144-[5-(4-Cyanophenyl)-2-pyrimidinyl]benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

247 mg of sodium are treated at room temperature with 10 ml of methanol. After 15 minutes the solution obtained is treated at room temperature with 1.58 g of 4-amidinobenzamide hydrochloride. A white suspension forms and this is treated dropwise at room temperature within 10 minutes with a solution of 1.42 g of 2-(4-cyanophenyl)-3-methoxyacrolein in 50 ml of methanol. The reaction mixture is stirred at room temperature for a further 2 hours and then suction filtered. The residue is washed with water, tetrahydrofuran and diethyl ether and dried in a high vacuum. 4-[5-(4-Cyanophenyl)-2-pyrimidinyl]benzamide is obtained.

Workup

  1. customAfter 15 minutes the solution obtained
  2. filtrationsuction filtered
  3. washThe residue is washed with water, tetrahydrofuran and diethyl ether
  4. customdried in a high vacuum

Sources & evidence

ORD record
ord-f2c4875e63134ec497c2dfd574b7b513
Source dataset
uspto-grants-1996_01
Patent number
US05486310

Reaction notes

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