1,1'-Carbonyldiimidazole → HCID 86680397, compound

HRID 1023156Notes

Reaction equation

HRID 1023156 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][C:3]=1[CH2:15][OH:16].C1N=CN([C:22](N2C=NC=C2)=[O:23])C=1>C1COCC1.O>[O:23]=[C:22]1[NH:1][C:2]2[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][C:3]=2[CH2:15][O:16]1

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86680398HCID 86680398, compound

Product 1

HCID 86680397HCID 86680397, compoundYield 13.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-amino-3-(hydroxymethyl)phenoxy)acetate (0.2 g, 0.888 mmol) in THF (5 mL) was added CDI (0.216 g, 1.332 mmol) at 0° C. and stirred at RT for 2 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer washed with brine, dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate as eluent to yield ethyl 2-((2-oxo-2,4-dihydro-1H-benzo[d][1,3]oxazin-6-yl)oxy)acetate (0.03 g, 13%). 1H NMR: 400 MHZ, DMSO-d6: δ 1.22 (t, J=7.20 Hz, 3H), 4.17 (q, J=6.80 Hz, 2H), 4.72 (s, 2H), 5.23 (s, 2H), 6.79-6.86 (m, 3H), 10.01 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-56692d6f69314ec5a1769251ceb1f9e9
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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