Water → 4-Dimethylamino-4-methoxybenzanilide

HRID 1197873Notes

Reaction equation

HRID 1197873 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](N)=[CH:5][CH:4]=1.C[N:11]([CH3:21])[C:12]1[CH:20]=[CH:19][C:15](C(Cl)=O)=[CH:14][CH:13]=1.[OH2:22].[N:23]1[CH:28]=CC=C[CH:24]=1>>[CH3:24][N:23]([CH3:28])[C:3]1([O:2][CH3:1])[CH:8]=[CH:7][C:6]([C:21]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:19][CH:20]=2)=[O:22])=[CH:5][CH2:4]1

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7732P-AnisidineHCID 44007824-(Dimethylamino)benzoyl chloride

Product 1

HCID 678489844-Dimethylamino-4-methoxybenzanilide

Procedure

201 g of p-anisidine were added to a suspension of 300 g of 4-dimethylamino-benzoic acid chloride in 1200 ml of pyridine and the mixture was stirred until dissolution. Then, the mixture was refluxed for 3 hours and after cooling to ambient temperature, the reaction medium was poured into 6 liters of iced water. The precipitate was separated and washed with water, then dried under reduced pressure to obtain 423 g of 4-dimethylamino-4-methoxybenzanilide melting at 173° C.

Workup

  1. temperatureThen, the mixture was refluxed for 3 hours
  2. customThe precipitate was separated
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-fa8ad52de21540929ac6d6624fcf6fed
Source dataset
uspto-grants-1994_01
Patent number
US05278180

Reaction notes

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