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

HRID 1247175Notes

Reaction equation

HRID 1247175 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[NH2:14].C(N(CC)CC)C.[C:23]([C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[NH:14][C:31](=[O:32])[C:30]1[CH:34]=[CH:35][C:27]([C:23]([CH3:25])([CH3:24])[CH3:26])=[CH:28][CH:29]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 743724-tert-Butylbenzoyl chlorideHCID 79336Dimethyl aminoterephthalateHCID 516892Sodium Bicarbonate

Product 1

HCID 9904721,4-Dimethyl 2-[[4-(1,1-dimethylethyl)benzoyl]amino]-1,4-benzenedicarboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customto come slowly to room temperature
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated
  5. dissolutionThe residue was redissolved in a minimum ether

Sources & evidence

ORD record
ord-6a2e912f0a624df4b1117793a3ef8a0a
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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