Benzoyl isothiocyanate → HCID 11572334, compound

HRID 1171790Notes

Reaction equation

HRID 1171790 reaction equation
C([N:9]=[C:10]=[S:11])(=O)C1C=CC=CC=1.[NH:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH2:17][NH:18][C:19]1[CH:23]=[CH:22][NH:21][C:20]=1[C:24]([O:26]CC)=O>C(Cl)Cl.CO>[NH:14]1[CH:15]=[CH:16][N:12]=[C:13]1[CH2:17][N:18]1[C:19]2[CH:23]=[CH:22][NH:21][C:20]=2[C:24](=[O:26])[NH:9][C:10]1=[S:11]

Participants

5

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 67068505HCID 67068505, compound

Product 1

HCID 11572334HCID 11572334, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Benzoyl isothiocyanate (0.19 mL, 1.41 mmol) was added to a stirred solution of ethyl 3-[(1H-imidazol-2-ylmethyl)amino]-1H-pyrrole-2-carboxylate (0.3 g, 1.28 mmol) in CH2Cl2 (4 mL) and methanol (2 mL) and the mixture was stirred at r.t. for 1 h. The solvent was evaporated in vacuo and the residue was dissolved in ammonia (7N in methanol, 7 mL) and heated at 80° C. for 1 h. The crude product was filtrated and purified by preparative HPLC, obtaining 0.110 g, (35%) of the title compound as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in ammonia (7N in methanol, 7 mL)
  3. temperatureheated at 80° C. for 1 h
  4. filtrationThe crude product was filtrated
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-5009216f70444e25a9273ced35e6fb2a
Source dataset
uspto-grants-2010_11
Patent number
US07829707B2

Reaction notes

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