p-Anisoyl chloride → N,N-Diethyl-para-anisamide

HRID 1768706Notes

Reaction equation

HRID 1768706 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C(N(CC)CC)C.[C:13](Cl)(=[O:22])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1>C(Cl)Cl>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[O:22])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8021DiethylamineHCID 8471Triethylamine

Product 1

HCID 231459N,N-Diethyl-para-anisamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of diethylamine (89.1 mL), triethylamine (120.2 mL) and CH2Cl2 (500 mL) cooled in an ice-bath was added dropwise p-anisoyl chloride (133.8 g) over 40 minutes. The reaction mixture was stirred at room temperature for 40 minutes, the mixture was filtered, washed with ether and the solvent was removed in vacuo. Ether was added, then water to the residue, then the organic layer was separate and washed with 5% NaOH, then in HCl, then brine and then was dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by kugelrohr distillation at 140°-180° C. under high vacuum to afford 163.8 g of 4-methoxy-N,N-diethylbenzamide, m.p. 40°-42° C.

Workup

  1. temperaturecooled in an ice-bath
  2. filtrationthe mixture was filtered
  3. washwashed with ether
  4. customthe solvent was removed in vacuo
  5. additionEther was added
  6. customwater to the residue, then the organic layer was separate
  7. washwashed with 5% NaOH
  8. dry with materialin HCl, then brine and then was dried over Na2SO4
  9. customThe solvent was removed in vacuo
  10. distillationthe residue was purified by kugelrohr distillation at 140°-180° C. under high vacuum

Sources & evidence

ORD record
ord-15302fb1ee49484581301408134ed9ad
Source dataset
uspto-grants-1995_01
Patent number
US05378720

Reaction notes

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