Water → 2-chloro-N,N-diethyl-4-methylbenzamide

HRID 365066Notes

Reaction equation

HRID 365066 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.[Cl:12]C1C=C(C=CC=1C)C(Cl)=O.[CH2:23]([NH:25][CH2:26][CH3:27])[CH3:24].O>S(Cl)(Cl)=O.CN(C)C=O.O1CCCC1>[Cl:12][C:8]1[CH:9]=[C:10]([CH3:11])[CH:2]=[CH:3][C:4]=1[C:5]([N:25]([CH2:26][CH3:27])[CH2:23][CH3:24])=[O:7]

Participants

8

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 788403-Chloro-4-methylbenzoic AcidHCID 184242113-Chloro-4-methylbenzoyl chloride

Product 1

HCID 8858472-chloro-N,N-diethyl-4-methylbenzamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of 32.2 g (0.19 mol) of 3-chloro-4-methylbenzoic acid in 100 mL of thionyl chloride is treated with 2 drops of dimethylformamide and heated on a steam bath for one hour. The clear amber solution is evaporated in vacuo several times with anhydrous toluene to give a clear amber oily residue. After dilution to a volume of 125 mL with anhydrous tetrahydrofuran, the 3-chloro-4-methyl-benzoyl chloride is added dropwise to a stirred solution of 43.3 mL (0.418 mol) of diethylamine in 300 mL anhydrous tetrahydrofuran under N2 at -5° C. The reaction mixture is allowed to come to room temperature over a 72 hour period then is treated with 300 mL water. The phases are separated; the aqueous phase is extracted with a total of 300 mL ethyl acetate. All organic phases are combined, washed with 300 mL of a saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo to give 40.0 g of a clear dark red oil. The infrared and proton nmr spectra are consistent with the desired structure. Gas-liquid chromatography analysis gives a purity of 96%.

Workup

  1. temperatureheated on a steam bath for one hour
  2. customThe clear amber solution is evaporated in vacuo several times with anhydrous toluene
  3. customto give a clear amber oily residue
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted with a total of 300 mL ethyl acetate
  6. washwashed with 300 mL of a saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93cd07e215884104aa96889423207bf2
Source dataset
uspto-grants-1986_08
Patent number
US04608079

Reaction notes

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