Water → 3-(2-Nitrobenzyl)-6-phenyl-[1,3]-oxazinan-2-one

HRID 553392Notes

Reaction equation

HRID 553392 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[CH2:6][NH:7][CH2:8][CH2:9][CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[OH:11])([O-:3])=[O:2].C(N(CC)CC)C.Cl[C:30](Cl)([O:32]C(=O)OC(Cl)(Cl)Cl)Cl.O>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:11][C:30]1=[O:32])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94429TriphosgeneHCID 674614753-(2-Nitrobenzylamino)-1-phenylpropanol

Product 1

HCID 674595203-(2-Nitrobenzyl)-6-phenyl-[1,3]-oxazinan-2-oneYield 129.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3-(2-Nitrobenzylamino)-1-phenylpropanol (3.00 g, 10.5 mmol), triethylamine (4.24 g, 42.0 mmol) were dissolved in toluene (50 ml). Under ice cooled condition, a solution in which triphosgene (1.24 g, 4.19 mmol) was dissolved in toluene (5 ml) was slowly added dropwise thereto and heated to reflux for six hours after stirred at room temperature for one hour. The reaction mixture was poured into water and, after standing to cool, extracted with ethyl acetate. The organic layer was washed with 0.1N hydrochloric acid water and then dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was washed with a mixture of ether-ethyl acetate (1:2) to obtain 3-(2-nitrobenzyl)-6-phenyl-[1,3]-oxazinan-2-one (1.70 g).

Workup

  1. additionwas slowly added dropwise
  2. temperatureheated
  3. temperatureto reflux for six hours
  4. temperatureto cool
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with 0.1N hydrochloric acid water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. washThe residue was washed with a mixture of ether-ethyl acetate (1:2)

Sources & evidence

ORD record
ord-ef7b56bbb7c4465581475e06a2593128
Source dataset
uspto-grants-2011_11
Patent number
US08048825B2

Reaction notes

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