Benzoyl isothiocyanate → HCID 22160582, compound

HRID 1089244Notes

Reaction equation

HRID 1089244 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C:13]1[N:17]([O:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:16]=[N:15][C:14]=1[C:30]([NH2:32])=[O:31]>CC(C)=O>[C:1]([NH:9][C:10]([NH:12][C:13]1[N:17]([O:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:16]=[N:15][C:14]=1[C:30]([NH2:32])=[O:31])=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 139898905-Amino-1-[3-(benzyloxy)propoxy]-1H-imidazole-4-carboxamide

Product 1

HCID 22160582HCID 22160582, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Benzoylisothiocyanate (1.0 ml, 7.6 mmol) in acetone (100 ml) was added to a solution of 5-amino-1-(3-benzyloxyprop-1-oxy)imidazole-4-carboxamide (2.0 g, 6.9 mmol) in hot acetone (200 ml). The solution was boiled under reflux for 6 hours, cooled, evaporated under reduced pressure, and the residue chromatographed on silica gel (eluted with chloroform and then chloroform-ethanol, 30:1), yielding the title compound (3.0 g, 96%), IR: υmax (KBr) 3470, 3300, 3130, 1670, 1610, 1535, 1495 cm-1. 1H NMR: δH [(CD3)2SO] 1.93 (2H, quintet, J=6.3 Hz, CH2CH2CH2), 3.54 (2H, t, J=6.3 Hz, CH2OCH2Ph), 4.39 (4H, m, CH2ON, CH2Ph), 7.12 (1H, CONH), 7.25 (6H, m, PhCH2, CONH), 7.54 (2H, t, 2 protons of PhCO), 7.68 (1H, t, 1 proton of PhCO), 8.10 (3H, m, H-2, 2 protons of PhCO), 11.95 (2H, br.s, 2 x NH).

Workup

  1. temperatureunder reflux for 6 hours
  2. temperaturecooled
  3. customevaporated under reduced pressure
  4. customthe residue chromatographed on silica gel (
  5. washeluted with chloroform

Sources & evidence

ORD record
ord-e4d02198c0664833a0456cb08adfaec5
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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