Acetic Acid → Ethyl 4-[4-(5-chloro-2-thienyl)-2-oxo-4-oxazolin-5-yl]butanoate

HRID 563105Notes

Reaction equation

HRID 563105 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](=O)[CH:8]([O:17][C:18]([O:20]C2C=CC=CC=2)=O)[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:32].C(O)(=O)C>O>[Cl:1][C:2]1[S:6][C:5]([C:7]2[NH:32][C:18](=[O:20])[O:17][C:8]=2[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 18174743Ethyl 6-(5-chloro-2-thienyl)-6-oxo-5-phenoxycarbonyloxyhexanoate

Product 1

HCID 18174756Ethyl 4-[4-(5-chloro-2-thienyl)-2-oxo-4-oxazolin-5-yl]butanoateYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 6-(5-chloro-2-thienyl)-6-oxo-5-phenoxycarbonyloxyhexanoate (30.5 g), ammonium acetate (28.6 g) and acetic acid (100 ml) was stirred with heating under reflux for 2 hours. The reaction mixture was poured into 500 ml of water, and the resulting solid precipitate was collected, washed with water and isopropyl ether and air-dried to give crystals of ethyl 4-[4-(5-chloro-2-thienyl)-2-oxo-4-oxazolin-5-yl]butanoate (13.6 g, 58%). Recrystallization from acetone-isopropyl ether gave pale yellow prisms. Melting point 95-96° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hours
  3. customthe resulting solid precipitate was collected
  4. washwashed with water and isopropyl ether
  5. customair-dried

Sources & evidence

ORD record
ord-1dc1de0d448147cfb99001ac689c2f57
Source dataset
uspto-grants-2011_11
Patent number
US08067453B2

Reaction notes

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