Sodium Bisulfate → 5-Ethyl-1,3-oxazolidin-2-one

HRID 1762278Notes

Reaction equation

HRID 1762278 reaction equation
O[CH:2]([N:4]1[CH2:8][CH:7]([CH2:9][CH3:10])[O:6][C:5]1=[O:11])[CH3:3].OS([O-])(=O)=O.[Na+]>>[CH:2]([N:4]1[CH2:8][CH:7]([CH2:9][CH3:10])[O:6][C:5]1=[O:11])=[CH2:3].[CH2:9]([CH:7]1[O:6][C:5](=[O:11])[NH:4][CH2:8]1)[CH3:10]

Participants

4

Reactant 2

HCID 516919Sodium BisulfateHCID 14474964HCID 14474964, compound

Product 2

HCID 137045895-Ethyl-1,3-oxazolidin-2-oneHCID 144749663-Ethenyl-5-ethyl-1,3-oxazolidin-2-one

Procedure

3-(1-Hydroxyethyl)-5-ethyl-2-oxazolidinone is prepared from 72 g (0.626 mole) of 5-ethyl-2-oxazolidinone by the procedure described in Example 1. A total of 96 g of 3-(1-hyroxyethyl)-5-ethyl-2-oxazolidinone is obtained (87 percent conversion). The 3-(1-hydroxyethyl)-5-ethyl-2-oxazolidinone is dehydrated in the hot tube filled with steel helices which is coated with a catalyst of NaHSO4. The dehydration is conducted at 260° C. under 40 mm Hg pressure. A dark red liquid (83 g) is collected which gives 64.6 g of N-vinyl-5-ethyl-2-oxazolidinone and 10.4 g of 5-ethyl-2-oxazolidinone upon fractionation. The yield is 87 percent based on 86 percent conversion of 5-ethyl-2-oxazolidinone.

Workup

  1. customis conducted at 260° C. under 40 mm Hg pressure
  2. customA dark red liquid (83 g) is collected which

Sources & evidence

ORD record
ord-2837480a0a1e448c9615fcb083fe76d5
Source dataset
uspto-grants-1989_05
Patent number
US04831153

Reaction notes

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