Dimethylformamide → Carbamic acid, octyl ester

HRID 2287985Notes

Reaction equation

HRID 2287985 reaction equation
[OH:1]C(CC)CN1C=C([N+]([O-])=O)N=C1[N+]([O-])=O.[CH2:17](N=C=O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C[N:29]([CH:31]=[O:32])C>C(OCC)C.[Cu]I>[C:31](=[O:32])([O:1][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[NH2:29]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 76616Octyl isocyanateHCID 4607421-(2,4-Dinitro-1H-imidazol-1-yl)butan-2-ol

Product 1

HCID 16240Carbamic acid, octyl esterYield 60%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

Procedure

To a heterogeneous mixture of 1-(2'-hydroxybutyl)-2,4-dinitroimidazole (500 mg, 2.17 mmol, Eur. J. Med. Chem. 24:631-633 (1989)) and 258 mg (2.60 mmol) of CuI in 10 mL of dry DMF was added 767 μL (4.34 mmol) of octyl isocyanate. The mixture was stirred for 2 h, diluted with 40 mL of ethyl ether and the organic solution was washed with water, dried over magnesium sulfate and concentrated. The crude product was purified by chromatography on silica gel (hexane:ethyl acetate, 6:1) to give 502 mg (60%) of n-octyl carbamate. 1H NMR (CDCl3) δ 0.86 (t, 3H), 1.11 (t, 3H), 1.28 (m, 10H), 1.40 (m, 2H), 1.75 (m, 2H), 3.05 (m, 2H), 4.42 (q, 1H), 4.75 (t, 1H), 4.90 (q, 1H), 5.10 (m, 1H), 7.88 (s, 1H); 13C NMR (CDCl3) δ 9.32, 14.01, 22.54, 25.10, 26.54, 29.06, 29.63, 31.69, 40.04, 41.08, 54.28, 72.65, 124.14, 155.20; MS 386 (M+)

Workup

  1. washthe organic solution was washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by chromatography on silica gel (hexane:ethyl acetate, 6:1)

Sources & evidence

ORD record
ord-2fcbee44e04b4bf0bd40148abd79929a
Source dataset
uspto-grants-2000_07
Patent number
US06087358

Reaction notes

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