Benzoyl isothiocyanate → HCID 11521960, compound

HRID 536113Notes

Reaction equation

HRID 536113 reaction equation
C([N:9]=[C:10]=[S:11])(=O)C1C=CC=CC=1.[Cl:12][C:13]1[CH:14]=[C:15]([NH:19][C:20]2[CH:24]=[CH:23][NH:22][C:21]=2[C:25]([O:27]CC)=O)[CH:16]=[CH:17][CH:18]=1>C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[C:15]([N:19]2[C:20]3[CH:24]=[CH:23][NH:22][C:21]=3[C:25](=[O:27])[NH:9][C:10]2=[S:11])[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanate2×HCID 67068489HCID 67068489, compound

Product 1

HCID 11521960HCID 11521960, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzoyl isothiocyanate (0.035 g, 0.22 mmol) in CH2Cl2 (0.5 mL) was added to ethyl 3-[(3-chlorophenyl)amino]-1H-pyrrole-2-carboxylate (0.052 g, 0.20 mmol) in CH2Cl2 (0.5 mL). The mixture was stirred at r.t. overnight. Additional benzoyl isothiocyanate (0.035 g+0.035 g+0.035 g) were added over 6 h and the reaction was continued stirring at 50° C. for 3 days. The solvent was removed in vacuo and the residue was dissolved in ammonia (7N in methanol, 4 mL). The reaction was heated at 50° C. for 2 h. The crude product was purified by preparative chromatography, obtaining 0.009 g (15%) of the title compound as a solid.

Workup

  1. stirringthe reaction was continued stirring at 50° C. for 3 days
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ammonia (7N in methanol, 4 mL)
  4. temperatureThe reaction was heated at 50° C. for 2 h
  5. customThe crude product was purified by preparative chromatography

Sources & evidence

ORD record
ord-7ff79d31525f492cab073e31d61a52ff
Source dataset
uspto-grants-2014_10
Patent number
US08859568B2

Reaction notes

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