2,4-Dimethoxyphenyl isocyanate → N'-(2.4-dimethoxyphenyl)-N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-N-heptylurea

HRID 374055

Reaction equation

HRID 374055 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:32][O:33][C:34]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:35]=1[N:42]=[C:43]=[O:44]>CCCCCC>[CH3:32][O:33][C:34]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:35]=1[NH:42][C:43](=[O:44])[N:24]([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][S:18][C:9]1[NH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 6016372,4-Dimethoxyphenyl isocyanateHCID 10048624N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-heptanamine

Product 1

HCID 19021744N'-(2.4-dimethoxyphenyl)-N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-N-heptylureaYield 82.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

To a solution of N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-1-heptanamine (0.75 g, 0.0017 mol), prepared according to the procedure of Example 1, Part D, in hexane (40 mL) was added, dropwise, a solution of 2,4-dimethoxyphenylisocyanate (0.358 g, 0.002 mol) in hexane (20 mL) and the reaction mixture was stirred at ambient temperature for 4.5 hours. The reaction mixture was concentrated under vacuum and the residue was chromatographed with 7:3 hexane-ethyl acetate. The resulting solid was triturated with hexane to give the title compound (0.83 g, 0.0014 mol) as a glassy solid. 1H NMR (CDCl3) δ7.7-7.1(m,10H), 6.8-6.1(m,3H), 3.8(s,3H), 3.7(s,3H), 3.45(s,1H), 3.4-3.3(m,2H), 3.2(t,2H,J=7Hz), 3.0(t,2H,J=7Hz), 1.8-1.1(m,16H), 0.9(t,3H,J=8Hz).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue was chromatographed with 7:3 hexane-ethyl acetate
  4. customThe resulting solid was triturated with hexane

Sources & evidence

ORD record
ord-c13bb4c81eaf4bdba3689c23a46ed01b
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Linked notes

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