Triethylamine → Benzanilide

HRID 1017808

Reaction equation

HRID 1017808 reaction equation
C(OC)(=O)[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH2:20][C:21]1[CH:36]=[CH:35][C:24](C(OCC2C=CC=CC=2)=O)=[CH:23][CH:22]=1.C(N(CC)CC)C>C(OCC)(=O)C.CN(C=O)C.C(Cl)Cl>[C:6]([NH:20][C:21]1[CH:36]=[CH:35][CH:24]=[CH:23][CH:22]=1)(=[O:8])[C:5]1[CH:4]=[CH:3][CH:2]=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 98488Benzyl p-aminobenzoateHCID 36144541,4-Benzenedicarboxylic acid, methyl ester

Product 1

HCID 7168BenzanilideYield 134.8%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of mono-methyl terephthalate (4.00 g, 22 mmol) in ethyl acetate (25 mL) and DMF (0.1 mL) was cooled in an ice bath and treated with oxalyl chloride (11 mL, 2N in CH2Cl2, 22 mmol) over 30 minutes. After stirring 2 hours at room temperature the solvent was removed on a rotary evaporator and the residue dissolved in CH2Cl2 (20 mL) and added to a solution of benzyl 4-aminobenzoate (5.00 g, 22 mmol) in CH2Cl2 (25 mL) and triethylamine (4.3 mL, 31 mmol) at −60° C. The reaction mixture was warmed to room temperature for 1 hour and then partitioned between water and ethyl acetate. The ethyl acetate layer was dried over sodium sulfate, filtered, and evaporated. The residue was recrystallized from t-butyl methyl ether to give 5.85 g of compound 8.

Workup

  1. customwas removed on a rotary evaporator
  2. dissolutionthe residue dissolved in CH2Cl2 (20 mL)
  3. temperatureThe reaction mixture was warmed to room temperature for 1 hour
  4. custompartitioned between water and ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was recrystallized from t-butyl methyl ether

Sources & evidence

ORD record
ord-9f8d21a2aa104ff597679c335e1f7e44
Source dataset
uspto-grants-2002_11
Patent number
US06479548B2

Linked notes

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