Dimethylformamide → 2-(4-Chlorophenyl)-3-methylbutanamide

HRID 1680135Notes

Reaction equation

HRID 1680135 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9](O)=[O:10])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.C[N:22](C)C=O>CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9]([NH2:22])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 16197Benzeneacetic acid, 4-chloro-alpha-(1-methylethyl)-HCID 65578Oxalyl chloride

Product 1

HCID 128981762-(4-Chlorophenyl)-3-methylbutanamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherCatalyst

Procedure

To a solution of 4.25 g (20 mmol) of 2-(4-chlorophenyl)-3-methylbutanoic acid in 30 ml of ether containing one drop of N,N-dimethylformamide is added dropwise 3.81 g (30 mmol) of oxalyl chloride. The solution is stirred at RT until gas evolution ceases. The solvent and excess oxalyl chloride are removed in vacuo and the residue is taken up in 30 ml of ether. This solution is then added dropwise at 0°-5° to 4.86 g (40 mmol) of a 14% w/w aqueous solution of ammonia. After stirring the mixture for 30 minutes at 0°-5°, the aqueous layer is removed. The ethereal solution is washed with water, dried over sodium sulfate, filtered and concentrated in vacuo to obtain 2-(4-chlorophenyl)-3-methylbutyramide.

Workup

  1. customThe solvent and excess oxalyl chloride are removed in vacuo
  2. additionThis solution is then added dropwise at 0°-5° to 4.86 g (40 mmol) of a 14% w/w aqueous solution of ammonia
  3. stirringAfter stirring the mixture for 30 minutes at 0°-5°
  4. customthe aqueous layer is removed
  5. washThe ethereal solution is washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aaaaf50224ff48339728ae24682256eb
Source dataset
uspto-grants-1981_06
Patent number
US04272449

Reaction notes

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