Carbonochloridic acid, cyclohexyl ester → HCID 10076535, compound

HRID 1109074Notes

Reaction equation

HRID 1109074 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.C(=O)(O)[O-].[Na+].[CH:37]1([O:43][C:44](Cl)=[O:45])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>C1(C)C=CC=CC=1>[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:44](=[O:45])[O:43][CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)[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

5

Reactant 3

HCID 83262Carbonochloridic acid, cyclohexyl esterHCID 516892Sodium BicarbonateHCID 10048624N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-heptanamine

Product 1

HCID 10076535HCID 10076535, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-1-heptanamine (0.87 g, 0.002 mol) and sodium bicarbonate (5%, 1 mL) in toluene (10 mL) at 0° was added, dropwise, a solution of cyclohexylchloroformate (0.32 g, 0.002 mol) in toluene (5 mL). The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The solvent was removed under vacuum. The residue (1.0 g) was chromatographed with 7:3 hexane-ethyl acetate to give the title compound (0.61 g, 0.0011 mol) as a yellow oil. 1H NMR (CDCl3) δ 11.1(bs,1H), 7.7-7.2(m,10H), 4.6(bs,1H), 3.3(t,2H,J=5.1 Hz), 3.2(t,2H,J=7.5 Hz), 3.0(t,2H,J=5.2 Hz), 1.9-1.2(m,26H), 0.9-0.8(m,3H).

Workup

  1. customThe solvent was removed under vacuum
  2. customThe residue (1.0 g) was chromatographed with 7:3 hexane-ethyl acetate

Sources & evidence

ORD record
ord-de04d7a87b124fb69e44e0f267e119ec
Source dataset
uspto-grants-1994_06
Patent number
US05318984

Reaction notes

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