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

HRID 1664509Notes

Reaction equation

HRID 1664509 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-dc4abe915f534d71b1ffa05a45e43a65
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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