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

HRID 553389Notes

Reaction equation

HRID 553389 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[CH2:6][NH:7][CH2:8][CH2:9][CH2:10][OH:11])([O-:3])=[O:2].C(N(CC)CC)C.Cl[C:24](Cl)([O:26]C(=O)OC(Cl)(Cl)Cl)Cl.O>C(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][O:11][C:24]1=[O:26])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94429TriphosgeneHCID 287156543-((2-Nitrobenzyl)amino)propan-1-ol

Product 1

HCID 674614643-(2-Nitrobenzyl)-[1,3]-oxazinan-2-oneYield 63%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

3-(2-Nitrobenzylamino)-1-propanol (1.03 g, 4.90 mmol) was dissolved in chloroform (20 ml) and the reaction solution was cooled to 0° C. Then triethylamine (1.98 g, 19.6 mmol), triphosgene (0.58 g, 1.95 mmol) were added thereto and the mixture was stirred at the same temperature for 1.5 hours. The reaction mixture was added with water and extracted with ethyl acetate and after the organic layer was washed with a saturated brine, it was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4) and 3-(2-nitrobenzyl)-[1,3]-oxazinan-2-one (0.29 g) was obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washafter the organic layer was washed with a saturated brine, it
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-6026ad72fdd640108e0a54a990fa2e25
Source dataset
uspto-grants-2011_11
Patent number
US08048825B2

Reaction notes

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