Hydrochloric Acid → N-(4-butyl-2-chlorophenyl)acetamide

HRID 1925712Notes

Reaction equation

HRID 1925712 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[Cl:15]N1C(=O)CCC1=O.Cl>CN(C)C=O>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:7]([Cl:15])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 77227Acetamide, N-(4-butylphenyl)-

Product 1

HCID 59180380N-(4-butyl-2-chlorophenyl)acetamideYield 103.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 67 (7.0 g; 36.6 mmol) and N-chlorosuccinimide (7.8 g; 58.6 mmol) was dissolved in N,N-dimethylformamide (70 mL). The reaction was heated at 70° C. for 6 hours, cooled to room temperature, then poured into aqueous hydrochloric acid (400 mL; 2M), and stirred for 15 minutes. The resulting precipitate was isolated by filtration and dried under vacuum to give the title product as an orange solid (8.54 g).

Workup

  1. temperaturecooled to room temperature
  2. customThe resulting precipitate was isolated by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-ad311ba304954a8f86fa6dafa422b20e
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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