P-Anisidine → HCID 57589835, compound

HRID 1783435Notes

Reaction equation

HRID 1783435 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=O.S([O-])([O-])(=O)=O.[Mg+2].C(N(CC)CC)C.[CH2:30]([O:37][CH2:38][C:39](Cl)=[O:40])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>ClCCl.C1(C)C=CC=CC=1>[CH2:30]([O:37][C@@H:38]1[C:39](=[O:40])[N:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C@@H:11]1[C:10]([O:14][CH2:15][CH3:16])=[O:13])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 5

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 70211Ethyl oxoacetateHCID 177085Benzyloxyacetyl chloride

Product 1

HCID 57589835HCID 57589835, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of p-anisidine (107, 5.4 mmol) in 10 ml anhydrous dichloromethane and 2 ml toluene were added ethyl glyoxylate (8.0 mmol, 50% solution in toluene) and anhydrous magnesium sulfate (3.0 g). The reaction mixture was heated at 70° C. for 3 h. Afterwards, the mixture was filtered and cooled to 0° C. with an ice/water bath. Triethylamine (10.8 mmol) and benzyloxyacetyl chloride (8.1 mmol) were added dropwise and the reaction mixture was stirred at room temperature for 18 h. Afterwards, it was concentrated in vacuo and triturated with ethyl ether and hexane to give compound 108 as a tan solid (69% yield). LS/MS M+H 356.2, calc. 356.12.

Workup

  1. filtrationAfterwards, the mixture was filtered
  2. temperaturecooled to 0° C. with an ice/water bath
  3. concentrationAfterwards, it was concentrated in vacuo
  4. customtriturated with ethyl ether and hexane

Sources & evidence

ORD record
ord-4eae807609d84181b764c388f79a50f0
Source dataset
uspto-grants-2009_03
Patent number
US07501404B2

Reaction notes

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