2,6-Dimethylaniline → N-(2,6-Dimethylphenyl)butanamide

HRID 1447818

Reaction equation

HRID 1447818 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[C:10](Cl)(=[O:14])[CH2:11][CH2:12][CH3:13]>CCOCC>[C:10]([NH:4][C:3]1[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=1[CH3:1])(=[O:14])[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 68962,6-DimethylanilineHCID 8855Butyryl chloride

Product 1

HCID 36333N-(2,6-Dimethylphenyl)butanamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 200 g. of 2,6-dimethylaniline in 2 l. of ether is cooled in an ice bath and to this 88 g. of butyryl chloride in 150 ml. of ether is added dropwise (over 21/2 hours). A white precipitate forms and the reaction mixture is allowed to stir at 0° C. for 1 hour longer and then 15 hours at room temperature. The reaction mixture is then evaporated in vacuo and the white solid residue is slurried in 1 l. of water, filtered and washed with water and dried to obtain N-butyryl-2,6-dimethylaniline (m.p. 134°-6° C.).

Workup

  1. custom15 hours
  2. customat room temperature
  3. customThe reaction mixture is then evaporated in vacuo
  4. filtrationof water, filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-acdccbd3ebbd43cdab5517bf568dbd80
Source dataset
uspto-grants-1979_12
Patent number
US04178387

Linked notes

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