Sulfuric Acid → 6-amino-1-(1H-benzimidazol-2-ylmethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

HRID 912665Notes

Reaction equation

HRID 912665 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][NH:11][C:12]([NH2:14])=[S:13].[O-]CC.[Na+].[C:19]([CH2:21][C:22](OCC)=[O:23])#[N:20].S(=O)(=O)(O)O>CCO.O>[NH2:20][C:19]1[N:11]([CH2:10][C:2]2[NH:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=2)[C:12](=[S:13])[NH:14][C:22](=[O:23])[CH:21]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7764Ethyl cyanoacetateHCID 2723922Sodium ethoxideHCID 86631117N-(1H-benzimidazol-2-ylmethyl)thiourea

Product 1

HCID 866311166-amino-1-(1H-benzimidazol-2-ylmethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-oneYield 30.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of N-(1H-benzimidazol-2-ylmethyl)thiourea (0.85 g, 4.1 mmol, obtained from Example 8(a)) in EtOH (10 mL) was added, dropwise, in portions during 7 h, sodium ethoxide (1M, 16.6 mL, 16.6 mmol) and a solution of ethyl cyanoacetate (1.76 mL, 16.6 mmol) in EtOH (10 mL) while the reaction was stirred at 80° C. After cooling to r.t. water (200 mL) was added followed by 2M sulphuric acid, the mixture was concentrated until precipitation occurred. The formed solid was collected by filtration, washed with water and dried to give the title compound (0.34 g, 30%) as a solid.

Workup

  1. additionwas added
  2. concentrationthe mixture was concentrated until precipitation
  3. filtrationThe formed solid was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6f3c7d293f3b43d5b9f4e644d16f9ec1
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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