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

HRID 1722524Notes

Reaction equation

HRID 1722524 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].[Cl:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>C(OCC)(=O)C.O>[Cl:16][CH2:17][CH2:18][C:19]([NH:4][C:3]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=1[CH3:1])=[O:20]

Participants

6

Reactant 3

HCID 68962,6-DimethylanilineHCID 11430Potassium CarbonateHCID 693643-Chloropropionyl chloride

Product 1

HCID 45508323-Chloro-2',6'-propionoxylidideYield 90.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 2,6-dimethylaniline (60.5 g) and potassium carbonate (45 g) is dissolved in a 3:1 mixture of ethyl acetate and water (1,200 ml). To the ice-cooled mixture, 100 ml of an ethyl acetate solution of 3-chloropropionyl chloride (52.5 ml) is added dropwise under agitation. The reaction mixture is stirred for 3 hours at room temperature and the aqueous layer is subsequently separated. The organic layer is washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and subsequently dried over Glauber's salt. Upon distilling off the solvent under vacuum, a colorless powder results. Recrystallization from ethanol provides a colorless needle in an amount of 96.5 g (yield: 90.8%). m.p. 131° C.

Workup

  1. additionis added dropwise under agitation
  2. customthe aqueous layer is subsequently separated
  3. washThe organic layer is washed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materiala saturated aqueous solution of sodium chloride, and subsequently dried over Glauber's salt
  5. distillationUpon distilling off the solvent under vacuum
  6. customa colorless powder results
  7. customRecrystallization from ethanol
  8. customprovides a colorless needle in an amount of 96.5 g (yield: 90.8%)

Sources & evidence

ORD record
ord-c44148e1d739459db2cf82aa30578d04
Source dataset
uspto-grants-1989_08
Patent number
US04855497

Reaction notes

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