Benzoyl isothiocyanate → HCID 23658375, compound

HRID 548780Notes

Reaction equation

HRID 548780 reaction equation
[CH3:1][C:2]([O:14][CH2:15][CH2:16][CH3:17])([CH3:13])[CH2:3][NH:4][C:5]1[N:6]=[CH:7][NH:8][C:9]=1[C:10]([NH2:12])=[O:11].C(N=[C:27]=[S:28])(=O)C1C=CC=CC=1>ClCCl>[CH2:15]([O:14][C:2]([CH3:1])([CH3:13])[CH2:3][N:4]1[C:5]2[N:6]=[CH:7][NH:8][C:9]=2[C:10](=[O:11])[NH:12][C:27]1=[S:28])[CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 67157931HCID 67157931, compound

Product 1

HCID 23658375HCID 23658375, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[(2-Methyl-2-propoxypropyl)amino]-1H-imidazole-5-carboxamide obtained from Example 2(c) was dissolved (0.19 g, 0.78 mmol) in 7 mL of dichloromethane. The obtained solution was stirred at ambient temperature. Benzoyl isothiocyanate (0.50 g, 3.1 mmol) was added in portions during 6 h. The reaction mixture was stirred over night and the solvent was then removed in vacuo. Ammonia in methanol (7 mL of 7 M solution) was added and the obtained solution was heated at 50° C. for 3 h and then at 80° C. for 3 h in a pressure flask. The cooled reaction mixture was concentrated and the crude product was purified by reverse phase HPLC. The product was obtained in 22% (48 mg) yield.

Workup

  1. stirringThe reaction mixture was stirred over night
  2. customthe solvent was then removed in vacuo
  3. additionAmmonia in methanol (7 mL of 7 M solution) was added
  4. temperaturethe obtained solution was heated at 50° C. for 3 h
  5. customThe cooled reaction mixture
  6. concentrationwas concentrated
  7. customthe crude product was purified by reverse phase HPLC
  8. customThe product was obtained in 22% (48 mg)
  9. customyield

Sources & evidence

ORD record
ord-0582d19dffc241129ec970895a39eba5
Source dataset
uspto-grants-2011_05
Patent number
US07943625B2

Reaction notes

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