Dimethylformamide → HCID 178518765, compound

HRID 536106Notes

Reaction equation

HRID 536106 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[NH:6][C:7]([CH2:9][NH:10][C:11]3[CH:15]=[CH:14][NH:13][C:12]=3[C:16]([O:18]CC)=O)=[N:8][C:4]=2[CH:3]=1.CN(C=O)C.C([N:36]=[C:37]=[S:38])(=O)C1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[NH:6][C:7]([CH2:9][N:10]3[C:11]4[CH:15]=[CH:14][NH:13][C:12]=4[C:16](=[O:18])[NH:36][C:37]3=[S:38])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 68284Benzoyl isothiocyanateHCID 178470386HCID 178470386, compound

Product 1

HCID 178518765HCID 178518765, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 3-{[(5-chloro-1H-benzimidazol-2-yl)methyl]amino}-1H-pyrrole-2-carboxylate (0.074 g, 0.23 mmol) in CH2Cl2 was stirred for 5 minutes. DMF (0.2 mL) was added to enhance solubility. Benzoyl isothiocyanate (0.045 g,0.28 mmol) was added and the mixture was stirred for 1 h then concentrated in vacuo. The crude intermediate was taken up in ammonia (7N in methanol, 2 mL) and was stirred at 70° C. for 1.5 h in a sealed vessel. After cooling to r.t. the precipitated product was collected by vacuum filtration, washed with diethyl ether and dried, obtaining 0.033 g (43%) of the title product as a white solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. stirringwas stirred at 70° C. for 1.5 h in a sealed vessel
  3. filtrationwas collected by vacuum filtration
  4. washwashed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-dd7894b72c4b4eaa8ae4105375770469
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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