Hydrochloric Acid → (6-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetic acid

HRID 1710661Notes

Reaction equation

HRID 1710661 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.Cl[CH2:13][C:14]([O:16]CC)=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C.[Li+].[OH-].C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]([CH2:13][C:14]([OH:16])=[O:15])[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7751Ethyl chloroacetateHCID 10796Cesium carbonateHCID 298586-Chloro-2,3-dihydrobenzoxazol-2-one

Product 1

HCID 776366(6-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetic acid

Reagents, catalysts & solvents 3

HCID 3939Lithium HydroxideSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

(6-Chloro-2-oxo-benzooxazol-3-yl)-acetic acid was prepared by heating 6-chloro-3H-benzooxazol-2-one and ethyl chloroacetate in the presence of cesium carbonate in DMF at 60° C. The crude residue was dissolved followed in 1N LiOH in THF and stirred at rt. The resultant mixture was acidified with 1N HCl to pH ˜1. The desired product precipitated out of solution and was isolated by filtration, and used directly in subsequent reactions without further purification.

Workup

  1. customThe desired product precipitated out of solution
  2. customwas isolated by filtration
  3. customused directly in subsequent reactions without further purification

Sources & evidence

ORD record
ord-7a96ee914095404aae96e68055f0de20
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

Loading…