Ethoxalyl chloride → Ethyl 2-[4-(4-chlorophenyl)-2-oxo-4-oxazolin-5-yl]-2-oxoacetate

HRID 567157Notes

Reaction equation

HRID 567157 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:13])[O:11][CH:12]=2)=[CH:4][CH:3]=1.Cl[C:15](=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>[Ti](Cl)(Cl)(Cl)Cl.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10](=[O:13])[O:11][C:12]=2[C:15](=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 114241254-(4-Chlorophenyl)-2,3-dihydro-1,3-oxazol-2-one

Product 1

HCID 18376466Ethyl 2-[4-(4-chlorophenyl)-2-oxo-4-oxazolin-5-yl]-2-oxoacetateYield 89%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Titanium tetrachloride(15.5 g) was added dropwise into a mixture of 4-(4-chlorophenyl)-4-oxazolin-2-one(4.00 g), ethyl chloroglyoxylate(5.58 g) and dichloromethane(30 ml) at room temperature. After stirring for 2 hours, the reaction mixture was poured into ice water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, and dried(MgSO4). The solvent was evaporated to give ethyl 2-[4-(4-chlorophenyl)-2-oxo-4-oxazolin-5-yl]-2-oxoacetate as crystals(5.38 g, 89%). This was recrystallized from ethyl acetate-hexane to give pale yellow prisms. mp 152-153° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water, and dried(MgSO4)
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b113f93dd4bb4dd48ec71b2ebe3e37d5
Source dataset
uspto-grants-2001_01
Patent number
US06177452B1

Reaction notes

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