Water → Ethyl 3-chloro-4-(4-methyl-2-oxo-oxazolidin-3-yl)-benzoate

HRID 2094318Notes

Reaction equation

HRID 2094318 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[NH:13][CH:14]([CH3:17])[CH2:15][OH:16])[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)CC)C.[C:25](Cl)(Cl)=[O:26].O>C1COCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[N:13]1[CH:14]([CH3:17])[CH2:15][O:16][C:25]1=[O:26])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

7

Reactant 4

HCID 962WaterHCID 6371PhosgeneHCID 8471TriethylamineHCID 67048695Ethyl 3-chloro-4-(2-hydroxy-1-methyl-ethylamino)-benzoate

Product 1

HCID 67048447Ethyl 3-chloro-4-(4-methyl-2-oxo-oxazolidin-3-yl)-benzoate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.50 g (1.94 mmol) ethyl 3-chloro-4-(2-hydroxy-1-methyl-ethylamino)-benzoate are placed in 30 ml THF together with 0.22 g (2.20 mmol) triethylamine and 1.10 ml (2.08 mmol) 20% phosgene solution in toluene is added with stirring at ambient temperature. The mixture is stirred for 1 hour at ambient temperature, then 1 ml of water is added and the mixture is stirred for another 10 minutes. The mixture is then evaporated down i. vac., combined with water and extracted with ethyl acetate. The combined organic phases are washed with water and sat. sodium chloride solution, dried over sodium sulphate and evaporated down i. vac.

Workup

  1. additionis added
  2. stirringThe mixture is stirred for 1 hour at ambient temperature
  3. stirringthe mixture is stirred for another 10 minutes
  4. customThe mixture is then evaporated down i
  5. extractionextracted with ethyl acetate
  6. washThe combined organic phases are washed with water and sat. sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. customevaporated down i

Sources & evidence

ORD record
ord-5c52d04752434d8795be15a4d5d4ad64
Source dataset
uspto-grants-2013_05
Patent number
US08445525B2

Reaction notes

Loading…