Dichloromethane → 1-(1H-Benzimidazol-2-ylmethyl)-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-one

HRID 536099Notes

Reaction equation

HRID 536099 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]1[CH:16]=[CH:15][NH:14][C:13]=1[C:17]([O:19]CC)=O.C(Cl)Cl.C([N:33]=[C:34]=[S:35])(=O)C1C=CC=CC=1>CO>[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[CH2:10][N:11]1[C:12]2[CH:16]=[CH:15][NH:14][C:13]=2[C:17](=[O:19])[NH:33][C:34]1=[S:35]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 68284Benzoyl isothiocyanateHCID 67068526Ethyl 3-[(1H-benzimidazol-2-ylmethyl)amino]-1H-pyrrole-2-carboxylate

Product 1

HCID 115729671-(1H-Benzimidazol-2-ylmethyl)-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-oneYield 168.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 3-[(1H-benzimidazol-2-ylmethyl)amino]-1H-pyrrole-2-carboxylate (0.33 g, 1.16 mmol) was added to CH2Cl2 (3 mL) and methanol was added until clear solution was obtained. The solution was stirred at r.t. for 1 h. Benzoyl isothiocyanate (0.73 mL, 0.46 mmol) was added and after stirring at r.t. for 30 minutes the mixture was concentrated. The residue was dissolved in ammonia (7N in methanol, 7 mL) and the mixture was heated at 80° C. in a sealed steel container for 2 h. After cooling to r.t. the precipated product was filtrated and washed through with methanol, diethyl ether and ethyl acetate, obtaining 0.23 g (66%) of the title compound as a white solid.

Workup

  1. additionwas added until clear solution
  2. customwas obtained
  3. stirringafter stirring at r.t. for 30 minutes the mixture
  4. concentrationwas concentrated
  5. dissolutionThe residue was dissolved in ammonia (7N in methanol, 7 mL)
  6. temperaturethe mixture was heated at 80° C. in a sealed steel container for 2 h
  7. temperatureAfter cooling to r.t. the precipated product
  8. filtrationwas filtrated
  9. washwashed through with methanol, diethyl ether and ethyl acetate

Sources & evidence

ORD record
ord-5a25b2e3741447f3b411647c5a0e41d0
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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