Ethyl isocyanate → HCID 23381347, compound

HRID 395969Notes

Reaction equation

HRID 395969 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:6]=CC=CC=1.[CH2:16]([N:18]=[C:19]=[O:20])[CH3:17].[O:21]1CCCC1>>[CH2:16]([NH:18][C:19]([NH:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:7][C@@H:1]2[CH2:6][O:21]2)=[CH:14][CH:13]=1)=[O:20])[CH3:17]

Participants

4

Reactant 3

HCID 8022Ethyl isocyanate2×HCID 8028TetrahydrofuranHCID 228604-Benzyloxyaniline

Product 1

HCID 23381347HCID 23381347, compound

Procedure

4-(Phenylmethoxy)-benzenamine (5.1 g, 25.5 mmol) was dissolved in anhydrous tetrahydrofuran and ethyl isocyanate (2.00 g, 28.1 mmol) added. The solution was heated to reflux. After 24 hours ethyl isocyanate (2.00 g, 28.1 mmol) was again added to the reaction mixture and refluxing continued for a further 24 hours. The reaction mixture was taken to dryness in vacuo and the residue purified by flash chromatography on silica gel Merck-60 (eluant: 3:1 hexane-ethyl acetate) to yield the title compound (6.3 g, 23.30 mmol).

Workup

  1. temperatureThe solution was heated to reflux
  2. temperaturerefluxing
  3. customthe residue purified by flash chromatography on silica gel Merck-60 (eluant: 3:1 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-76bc37e8cc2d4f378daf469ab3971e96
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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