Methyl Isocyanate → HCID 10390966, compound

HRID 374057

Reaction equation

HRID 374057 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 10390966HCID 10390966, compoundYield 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) δ7.6-7.2(m,11H), 4.35-2.7(m,9H), 1.9-1.2(m,16H), 0.9(t,3H,J=8Hz).

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-7fbf014c12194398ab3d5a592a2a4fd4
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Linked notes

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