Methyl Isocyanate → N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-N-heptyl-N'-methylurea

HRID 1109059Notes

Reaction equation

HRID 1109059 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][N:33]=[C:34]=[O:35]>CCCCCC>[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:34]([NH:33][CH3:32])=[O:35])[NH:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 10048624N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-heptanamine

Product 1

HCID 10390966N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-N-heptyl-N'-methylureaYield 67.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-1-heptanamine (0.30 g, 0.0007 mol) in hexane (15 mL) was added methylisocyanate (0.06 mL, 0.057 g, 0.001 mol) and the reaction mixture was stirred at ambient temperature for 18 hours. The reaction mixture was concentrated under vacuum and the residue was chromatographed with 1:1 hexane-ethyl acetate . The resulting oil was triturated with hexane to give the title compound (0.23 g, 0.00047 mol) as a white solid, mp 93°-96°.1H NMR (CDCl3) δ 7.6-7.2(m, 11H), 4.35-2.7(m, 9H), 1.9-1.2(m, 16H), 0.9(t,3H, J=8 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was chromatographed with 1:1 hexane-ethyl acetate
  3. customThe resulting oil was triturated with hexane

Sources & evidence

ORD record
ord-21794c17fa5a4d8291e3b526f81df537
Source dataset
uspto-grants-1994_06
Patent number
US05318984

Reaction notes

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