Water → HCID 54568712, compound

HRID 1195915Notes

Reaction equation

HRID 1195915 reaction equation
[C:1]1([C:7]2[O:11][C:10]([CH2:12][NH:13][OH:14])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][N:16]=[C:17]=[O:18].C(OCC)C.O>O1CCCC1>[OH:14][N:13]([CH2:12][C:10]1[O:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][CH:9]=1)[C:17]([NH:16][CH3:15])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 12228Methyl IsocyanateHCID 10655258HCID 10655258, compound

Product 1

HCID 54568712HCID 54568712, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(5-phenylfur-2-yl)methyl hydroxylamine (0.5 g, 2.64 mmol) in tetrahydrofuran (30 mL) was added methylisocyanate (0.24 mL, 3.97 mmol) dropwise at room temperature under nitrogen while stirring. The reaction was stirred for 20 h and ethyl ether (100 mL) and water (100 mL) was added. The organic layer was separated, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated in vacuo, to give a solid (0.58 g). Purification by chromatography (silica gel, 2% methanol in dichloromethane) gave the desired product (0.28 g), mp 135°-139° C.; NMR (300 MHz, DMSO-d6): 2.63 (3H, d, J=5.4 Hz), 4.53 (2H, s), 6.38 (1H, d, J=3.3 Hz), 6.87 (1H, d, J =3.3 Hz), 7.03 (1H, q, J=5.4 Hz), 7.24-7.30 (1H, m), 7.38-7.45 (2H, m), 7.38-7.45 (2H, m), 7.62-7.68 (2H, m), 9.40 (1H, s); MS (CI-NH3): M+H=247; Analysis Calculated for C13H14N2O3 : C, 63.40; H, 5.73, N, 11.38; Found C, 63.29; H, 5.76; N, 11.34.

Workup

  1. stirringThe reaction was stirred for 20 h
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4b177ba6c4344f3a877b1d615b5c0d7
Source dataset
uspto-grants-1992_05
Patent number
US05112848

Reaction notes

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