Benzoyl isothiocyanate → 4-[[(Benzoylamino)carbonothioyl](pentyl)amino]-1H-imidazole-5-carboxamide

HRID 2368552Notes

Reaction equation

HRID 2368552 reaction equation
[CH2:1]([NH:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12]([NH2:14])=[O:13])[CH2:2][CH2:3][CH2:4][CH3:5].[C:15]([N:23]=[C:24]=[S:25])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[C:15]([NH:23][C:24]([N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12]([NH2:14])=[O:13])=[S:25])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 57600193HCID 57600193, compound

Product 1

HCID 576001664-[[(Benzoylamino)carbonothioyl](pentyl)amino]-1H-imidazole-5-carboxamideYield 139.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(pentylamino)-1H-imidazole-5-carboxamide (4.0 g, 0.020 mol) in DCM (50 mL) was added benzoyl isothiocyanate (3.3 mL, 0.024 mol). After being stirred overnight, the solid formed was filtered to give the crude product (10 g, ca 60% purity, 80% yield). This product was used for next step without further purification. LCMS calculated for C17H22N5O2S (M+H): 360.1. Found: 360.1.

Workup

  1. customthe solid formed
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-9980cd7d7bf745de8daa2d0dec0ace13
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

Loading…