Phenyl isocyanate → N-hydroxy-N-(1-(5-methylfur-2-yl)ethyl)-N'-phenyl urea

HRID 1195909Notes

Reaction equation

HRID 1195909 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][C:11]1[O:15][C:14]([CH:16]([NH:18][OH:19])[CH3:17])=[CH:13][CH:12]=1>C1COCC1>[OH:19][N:18]([CH:16]([C:14]1[O:15][C:11]([CH3:10])=[CH:12][CH:13]=1)[CH3:17])[C:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:9]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 10654307N-(1-(5-methyl-fur-2-yl)ethyl) hydroxylamine

Product 1

HCID 54062848N-hydroxy-N-(1-(5-methylfur-2-yl)ethyl)-N'-phenyl ureaYield 30.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of phenyl isocyanate (0.87 mL, 8.0 mmol) in 10 mL THF was added N-(1-(5-methyl-fur-2-yl)ethyl) hydroxylamine (0.50 g, 4.0 mmol) in 3 mL THF. The reaction was stirred 1 h at room temperature and was quenched with saturated ammonium chloride solution (25 mL). The aqueous layer was extracted with ethyl acetate (3×10 mL) and the organic layer was washed with brine (1×20 mL). The solution was dried with MgSO4, filtered and evaporated. Chromatography (silica gel, 30% ether/hexanes) gave 0.32 g of desired product; m.p.=109°-110° C.; 1H NMR (300 MHz, DMSO-d6) 9.43 (bs, 1H), 8.97 (bs, 1H), 7.62 (dd, J=1.50, 8.71 Hz, 2H), 7.25 (m, 2H), 6.96 (m, 1H), 6.15 (d, J=3.00 Hz, 1H), 5.38 (q, J=6.9, 17.4 Hz, 1H), 2.19 (s, 3H), 1.39 (d, J=6.30 Hz, 3H); MS (M+H)+ =261; Analysis calc'd for C14H16N2O3 : C, 64.59; H, 6.20; N, 10.77. Found: C, 64.00; H, 6.12; N, 10.60.

Workup

  1. customwas quenched with saturated ammonium chloride solution (25 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×10 mL)
  3. washthe organic layer was washed with brine (1×20 mL)
  4. dry with materialThe solution was dried with MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6d8f0408039e488e89e6625067a3b607
Source dataset
uspto-grants-1992_05
Patent number
US05112848

Reaction notes

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