Benzoyl isothiocyanate → HCID 86631119, compound

HRID 912668Notes

Reaction equation

HRID 912668 reaction equation
Cl.Cl.[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH:12]([NH2:14])[CH3:13].CCN(C(C)C)C(C)C.C([N:32]=[C:33]=[S:34])(=O)C1C=CC=CC=1>C(Cl)Cl>[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH:12]([NH:14][C:33]([NH2:32])=[S:34])[CH3:13]

Participants

5

Reactant 3

HCID 68284Benzoyl isothiocyanateHCID 81531DiisopropylethylamineHCID 1732547574461-35-1

Product 1

HCID 86631119HCID 86631119, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1-(1H-Benzoimidazol-2-yl)-ethylamine dihydrochloride (0.50 g, 2.1 mmol) in CH2Cl2 (10 mL) was added DIPEA (0.74 mL, 4.3 mmol). After 5 minutes benzoyl isothiocyanate (0.32 mL, 2.4 mmol) was added and the reaction mixture was stirred for 2.5 h, followed by evaporation in vacuo. Ammonia (7M in MeOH, 20 mL) was then added and the reaction was stirred another 2.5 h. The excess ammonia was removed in vacuo and CH2Cl2 (10 mL) was added, the solid was collected by filtration giving the title compound (0.33 g, 70%). MS (ESI) m/z 221 (M+1).

Workup

  1. customfollowed by evaporation in vacuo
  2. additionAmmonia (7M in MeOH, 20 mL) was then added
  3. stirringthe reaction was stirred another 2.5 h
  4. customThe excess ammonia was removed in vacuo and CH2Cl2 (10 mL)
  5. additionwas added
  6. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-c27561dbf53a493c8a030b4e6d96b91c
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

Loading…