Water → 6-Methyl-3-(2-nitrobenzyl)-[1,3]-oxazepan-2-one

HRID 553395Notes

Reaction equation

HRID 553395 reaction equation
[CH3:1][CH:2]([CH2:5][CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])[CH2:3][OH:4].C(N(CC)CC)C.Cl[C:26](Cl)([O:28]C(=O)OC(Cl)(Cl)Cl)Cl.O>C1(C)C=CC=CC=1>[CH3:1][CH:2]1[CH2:3][O:4][C:26](=[O:28])[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94429TriphosgeneHCID 674613512-Methyl-4-(2-nitrobenzylamino)butanol

Product 1

HCID 674620256-Methyl-3-(2-nitrobenzyl)-[1,3]-oxazepan-2-oneYield 89.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2-Methyl-4-(2-nitrobenzylamino)butanol (5.00 g, 21.0 mmol), triethylamine (8.49 g, 84.1 mmol) were dissolved in toluene (50 ml). Under ice cooled condition, a solution in which triphosgene (2.50 g, 8.42 mmol) was dissolved in toluene (10 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 0.1 N hydrochloric acid water and then 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=2:1) to obtain 6-methyl-3-(2-nitrobenzyl)-[1,3]-oxazepan-2-one (2.00 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 0.1 N hydrochloric acid water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-92a8094a87f248578ef06b3fd02e8e31
Source dataset
uspto-grants-2011_11
Patent number
US08048825B2

Reaction notes

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