Phosgene → 3-tert-Butyl-5-(4-nitrophenyl)-1,3-oxazolidin-2-one

HRID 1248155Notes

Reaction equation

[C:1]([NH:5][CH2:6][CH:7]([OH:17])[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:18](Cl)(Cl)=[O:19]>C(Cl)Cl.C1C=CC=CC=1>[C:1]([N:5]1[CH2:6][CH:7]([C:8]2[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=2)[O:17][C:18]1=[O:19])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -5 °C

Procedure

In 270 ml of CH2Cl2, 12.97 g of α-[(tert-butylamino)methyl]-p-nitrobenzyl alcohol is dissolved. The solution is cooled to -5° C. and 54 ml of 12.5% phosgene in benzene is added slowly. After the addition is completed, the mixture is stirred for 3.5 hours and poured on ice. The organic phase is separated, and the aqueous layer is extracted with CH2Cl2 (2×100 ml). The combined organic layers are washed with saturated NaHCO3 solution (2×250 ml), 100 ml of H2O and dried over MgSO4. The solution is evaporated to dryness to give 16.3 g, which is recrystallized from MeOH twice to afford 12.58 g of 3-tert-butyl-5-(p-nitrophenyl)-2-oxazolidinone, mp 123°-125° C. This product (10 g) is dissolved in 200 ml of MeOH and hydrogenated over 6 g of Raney nickel at 51 p.s.i.g at 40° C. to give, after filtration and evaporation, 8.21 g of 5-(p-aminophenyl)-3-tert-butyl-2-oxazolidinone, mp 125°-129° C.

Workup

additionAfter the addition
additionpoured on ice
customThe organic phase is separated
extractionthe aqueous layer is extracted with CH2Cl2 (2×100 ml)
washThe combined organic layers are washed with saturated NaHCO3 solution (2×250 ml), 100 ml of H2O
dry with materialdried over MgSO4
customThe solution is evaporated to dryness
customto give 16.3 g, which
customis recrystallized from MeOH twice

Sources & evidence

ORD record: ord-53cd269e69164be494484860215257ad
Source dataset: uspto-grants-1985_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04522822

Reaction notes

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