Hydrochloric Acid → 1,4-Dimethyl 2-[[4-(1,1-dimethylethyl)benzoyl]amino]-1,4-benzenedicarboxylate

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Reaction Steps

Into 200 mL methylene chloride was dissolved 10.45 g (50 mmol) 2-aminoterephthalic acid dimethyl ester. The solution was cooled in an ice bath, and 7.73 mL (55 mmol) triethylamine was added, followed by 10.76 mL 4-tert-butylbenzoyl chloride in 50 mL methylene chloride dropwise. The mixture was allowed to come slowly to room temperature, and after 16 h the mixture was shaken with 200 mL cold dilute HCl and 200 mL satd NaHCO3. The organic layer was dried (MgSO4) and evaporated. The residue was redissolved in a minimum ether, giving 13.5 g (73%) of crystalline desired intermediate.

Provenance & Evidence