Hydrochloric Acid → HCID 11361709, compound

HRID 898354Notes

Reaction equation

HRID 898354 reaction equation
Cl[C:2]([N:4]=[C:5]=[O:6])=[O:3].[CH2:7]([C:14]1[C:18]2[CH:19]=[CH:20][C:21](/[C:23](/[CH2:28][CH3:29])=[CH:24]\[CH2:25][NH:26][OH:27])=[CH:22][C:17]=2[O:16][C:15]=1[CH2:30][CH3:31])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C1COCC1>[CH2:7]([C:14]1[C:18]2[CH:19]=[CH:20][C:21](/[C:23](/[CH2:28][CH3:29])=[CH:24]\[CH2:25][N:26]3[C:5](=[O:6])[NH:4][C:2](=[O:3])[O:27]3)=[CH:22][C:17]=2[O:16][C:15]=1[CH2:30][CH3:31])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 119708Isocyanatocarbonyl chlorideHCID 86597377HCID 86597377, compound

Product 1

HCID 11361709HCID 11361709, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-7.5 °C

Procedure

A solution of chlorocarbonyl isocyanate (0.31 mL; 3.88 mmol) in THF (5 mL) was added dropwise to the solution of Z-N-[3-(3-Benzyl-2-ethyl-benzofuran-6-yl)-pent-2-enyl]-hydroxylamine (1.3 g; 3.88 mmol) in THF (25 mL) at −10° C. The mixture was stirred for 1 hour at −10 to −5° C., and at 0° C. for 30 minutes, then poured over cold 1N HCl solution and extracted with ethyl acetate (3×50 mL). The organic extracts were combined, dried over anhydrous magnesium sulfate and solvent evaporated. The residue was purified by flash chromatography over acid-treated silica gel using 2-5% ethyl acetate in hexane as an eluent. The title compound was obtained (0.82 g) as a white solid. mp: 118-120° C. Mass spectrum (APCI, [M+H]+) m/z 405. 1HNMR (400 MHz, DMSO-d6): δ 0.88 (t, 3H, J=7.32 Hz), 1.23 (t, 3H, J=7.56 Hz), 2.42 (q, 2H, J=7.80 Hz), 2.87 (q, 2H, J=7.32 Hz), 3.98 (s, 2H), 4.12 (d, 2H, J=6.83 Hz), 5.51 (t, 1H, J=6.59 Hz), 6.96 (dd, 1H, J=8.05, 1.46 Hz) 7.14-7.19 (m, 1H), 7.24-7.28 (m, 3H), 7.30 (d, 1H, J=1.0 Hz), 7.37 (d, 1H, J=7.81 Hz), 12.3 (s, 1H). Elemental Analysis for C24H24N2O4: Calculated: C, 71.27; H, 5.98, N, 6.93. Found: C, 71.17; H, 6.14, N, 6.83.

Workup

  1. waitat 0° C. for 30 minutes
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate and solvent
  4. customevaporated
  5. customThe residue was purified by flash chromatography
  6. additionover acid-treated silica gel using 2-5% ethyl acetate in hexane as an eluent

Sources & evidence

ORD record
ord-9a1507868fcf4e3a90d0ea23acda29f8
Source dataset
uspto-grants-2008_04
Patent number
US07351726B2

Reaction notes

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