2,6-Dimethylaniline → 3-Chloro-2',6'-propionoxylidide

HRID 1059128Notes

Reaction equation

HRID 1059128 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C(OC(C)C)(C)C.[Cl:17][CH2:18][CH2:19][C:20](Cl)=[O:21]>O>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][C:20](=[O:21])[CH2:19][CH2:18][Cl:17]

Participants

5

Reactant 3

HCID 68962,6-DimethylanilineHCID 7914Diisopropyl EtherHCID 693643-Chloropropionyl chloride

Product 1

HCID 45508323-Chloro-2',6'-propionoxylidideYield 59.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2 l three-necked flask, is charged with 121.8 g of 2,6-dimethylaniline, 300 ml of isopropyl ether and 150 ml of water. 126.5 g of 3-chloropropanoyl chloride are added at a rate such that the internal temperature is between 5 and 10° C. At the end of the addition, the reaction medium is stirred for 3 h. The precipitate formed is filtered off with suction, washed with isopropyl ether and then with water and finally dried. 126 g of white crystals are obtained.

Workup

  1. customis between 5 and 10° C
  2. additionAt the end of the addition
  3. customThe precipitate formed
  4. filtrationis filtered off with suction
  5. washwashed with isopropyl ether
  6. dry with materialwith water and finally dried

Sources & evidence

ORD record
ord-a3e4a30f87d2437c833fc64f17029281
Source dataset
uspto-grants-2003_02
Patent number
US06518458B1

Reaction notes

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