Diethyl Ether → HCID 11052455, compound

HRID 369179Notes

Reaction equation

HRID 369179 reaction equation
S(Cl)(Cl)=O.O[CH2:6][CH2:7][NH:8][C:9]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][CH:12]=1)=[O:10].C(OCC)C.[OH-].[Na+]>CO>[O:10]1[CH2:6][CH2:7][N:8]=[C:9]1[C:11]1[CH:20]=[CH:19][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium Hydroxide2×HCID 24386Thionyl ChlorideHCID 4610719HCID 4610719, compound

Product 1

HCID 11052455HCID 11052455, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.2 ml of thionyl chloride was added to 2.23 g of methyl 4-(2-hydroxyethyl)aminocarbonylbenzoate. The mixture was stirred for 15 minutes. Thereto was added 10 ml of diethyl ether. The reaction mixture was added to 20 ml of a 5 N aqueous sodium hydroxide solution being cooled with an ice-methanol cryogen. The mixture was stirred for a while. The resulting precipitate was collected by filtration and water-washed to obtain a white powder. The powder was dissolved in 20 ml of methanol. Thereto was added 4 ml of 5 N sodium hydroxide. The mixture was stirred at 40° C. for 15 minutes and then concentrated under reduced pressure. To the residue was added ice water. The mixture was made acidic with acetic acid. The resulting crystals were collected by filtration, washed with water and methanol in this order, and dried to obtain 1.6 g of 4-(2-oxazolin-2-yl)benzoic acid as a white powder.

Workup

  1. stirringThe mixture was stirred for a while
  2. filtrationThe resulting precipitate was collected by filtration and water-
  3. washwashed
  4. customto obtain a white powder
  5. stirringThe mixture was stirred at 40° C. for 15 minutes
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue was added ice water
  8. filtrationThe resulting crystals were collected by filtration
  9. washwashed with water and methanol in this order
  10. customdried

Sources & evidence

ORD record
ord-45ea1f3d797e4d39ad11b7487936dc17
Source dataset
uspto-grants-2000_10
Patent number
US06136826

Reaction notes

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