Hydrochloric Acid → Phenacetin

HRID 1045827Notes

Reaction equation

HRID 1045827 reaction equation
[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)[CH3:2].C(N(CC)CC)C.[C:18](OC(=O)C)(=[O:20])[CH3:19].Cl>ClCCl>[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:18](=[O:20])[CH3:19])=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 90764-Ethoxyaniline

Product 1

HCID 4754Phenacetin

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Ethoxyaniline (40 g, 0.29 mol) and triethylamine (61 mL, 0.44 mol) were dissolved in dichloromethane (200 mL). Acetic anhydride (30 mL, 0.32 mol) was added in drops thereto, and the mixture was stirred for 1 h at 0° C. to room temperature. 1N hydrochloric acid solution was added, and the reaction mixture was extracted with ethyl acetate, washed with sodium chloride solution, and dried over anhydrous magnesium sulfate to give the title compound.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-011b25d47a5f490ab94b6595c4d67a2c
Source dataset
uspto-grants-2013_10
Patent number
US08569307B2

Reaction notes

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