Hydrochloric Acid → Methyl 4-(diethylcarbamoyl)benzoate

HRID 1934767Notes

Reaction equation

HRID 1934767 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)=[O:4].C(Cl)(=O)C(Cl)=O.[CH2:20]([NH:22][CH2:23][CH3:24])[CH3:21].Cl>C(Cl)Cl.CN(C)C=O>[CH2:20]([N:22]([CH2:23][CH3:24])[C:9]([C:8]1[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:13][CH:12]=1)=[O:11])[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 15513Monomethyl terephthalateHCID 65578Oxalyl chloride

Product 1

HCID 14434573Methyl 4-(diethylcarbamoyl)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

In 120 ml of methylene chloride was suspended 6.0 g of 4-(methoxycarbonyl)-benzoic acid, to which were added 3.5 ml of oxalyl chloride and 0.05 ml of N,N-dimethylformamide at 0-5° C. After a reaction at the same temperature as above for 3 hours, the mixture was stirred at ambient temperature for 24 hours. Then, a 90.7 g portion of the reaction mixture was taken out, and 6.9 ml of diethylamine was added thereto. The mixture was stirred at ambient temperature for 3 hours, and then poured into ice water. pH was adjusted to 1.0 with 6 mol/L hydrochloric acid, and the organic layer was separated. The organic layer was washed successively with water, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Thus, 5.89 g of methyl 4-[(diethylamino)carbonyl]-benzoate was obtained as a red oily product.

Workup

  1. customAfter a reaction at the same temperature as above for 3 hours
  2. stirringThe mixture was stirred at ambient temperature for 3 hours
  3. customthe organic layer was separated
  4. washThe organic layer was washed successively with water, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4ee0851a61d2444aa2dce0bd25e3ffa8
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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