2,5-Dimethoxyaniline → HCID 531990, compound

HRID 861920Notes

Reaction equation

HRID 861920 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][O:12][C:13]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:14]=1[NH2:15].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[CH3:11][O:12][C:13]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:14]=1[NH:15][C:8](=[O:9])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 76132,5-DimethoxyanilineHCID 7679Phenylacetyl chlorideHCID 10340Sodium Carbonate

Product 1

HCID 531990HCID 531990, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of phenylacetyl chloride (1.07 g, 6.6 mmol) in dry benzene (7 ml) was added drop by drop for 10 minutes to a cooled solution of 2,5-dimethoxyaniline (1 g, 6.5 mmol) in dry benzene (7 ml). The reaction mixture was agitated at room temperature for 1 hour and then the reaction was stopped with cold 24% aqueous sodium carbonate (10 ml.) After vigorously agitating the two-phase system for 30 minutes, the benzene layer was separated and the aqueous phase was extracted with ether (3×50 ml). The combined organic layers were dried over sodium sulfate and evaporated and the residue was crystallized from petroleum ether, yielding 1.61 g 91%) of N-(2',5'-dimethoxyphenyl)-2-phenylacetamide. m.p. 85° C. (petroleum ether).

Workup

  1. stirringAfter vigorously agitating the two-phase system for 30 minutes
  2. customthe benzene layer was separated
  3. extractionthe aqueous phase was extracted with ether (3×50 ml)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customevaporated
  6. customthe residue was crystallized from petroleum ether

Sources & evidence

ORD record
ord-b946f2797e6842bab162f83fa4b3d0f5
Source dataset
uspto-grants-1998_02
Patent number
US05716963

Reaction notes

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