Acetic Anhydride → HCID 3432986, compound

HRID 1109987Notes

Reaction equation

HRID 1109987 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH2:8])[CH:7]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH:8][C:16](=[O:18])[CH3:17])[CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 667385-Chloro-2-phenoxyaniline

Product 1

HCID 3432986HCID 3432986, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirring compound of the title compound of Example 9 (5.0 g, 23 mmol) in pyridine (50 mL) was added acetic anhydride (2.75 g, 27 mmol), and the resulting solution was stirred for 3 hours. The solvent was removed under reduced pressure and the residue was dissolved in CHCl3 (300 mL) and extracted with HCl (1M, 3×150 mL), NaHCO3 (saturated, 3×150 mL), dried (MqSO4) and evaporated to yield an oil. The material was chromatographed (MPLC, 1:1 EtOAc:hexane) to yield 4.52 g of a yellow oil. This material was employed in Example 11 without further purication.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in CHCl3 (300 mL)
  3. extractionextracted with HCl (1M, 3×150 mL), NaHCO3 (saturated, 3×150 mL)
  4. customdried (MqSO4)
  5. customevaporated
  6. customto yield an oil
  7. customThe material was chromatographed (MPLC, 1:1 EtOAc:hexane)

Sources & evidence

ORD record
ord-1fe5d7cbf35945baa16c78b6ea97da8c
Source dataset
uspto-grants-1994_06
Patent number
US05324722

Reaction notes

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