Dicyclohexylcarbodiimide → Dimethyl 2-((2,4-dichlorophenyl)acetylamino)terephthalate

HRID 1699876

Reaction equation

HRID 1699876 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[CH2:24][C:25](O)=[O:26].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[CH2:24][C:25]([NH:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[O:26]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 79336Dimethyl aminoterephthalateHCID 882092,4-Dichlorophenylacetic acid

Product 1

HCID 22388140Dimethyl 2-((2,4-dichlorophenyl)acetylamino)terephthalateYield 64.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of dimethyl 2-aminoterephthalate (2.09 g), 2,4-dichlorophenylacetic acid (2.05 g), N,N-dimethylaminopyridine (1.32 g) and dicyclohexylcarbodiimide (2.22 g) in tetrahydrofuran (20 ml) was stirred at room temperature for 2 hr and then at 80° C. for 4 hr. After cooling, the precipitate was filtered off and the filtrate was washed with 1N hydrochloric acid. Chloroform mixture was added to the obtained organic layer, and the mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and dried over sodium sulfate. The solvent was distilled away and the residue was washed with water and methanol to give the object compound (2.54 g) as white crystals.

Workup

  1. waitat 80° C. for 4 hr
  2. temperatureAfter cooling
  3. filtrationthe precipitate was filtered off
  4. washthe filtrate was washed with 1N hydrochloric acid
  5. additionChloroform mixture was added to the obtained organic layer
  6. washthe mixture was washed with a saturated aqueous sodium hydrogencarbonate solution
  7. dry with materialdried over sodium sulfate
  8. distillationThe solvent was distilled away
  9. washthe residue was washed with water and methanol

Sources & evidence

ORD record
ord-6bffbc440b8d49c0904d168bfbcb841b
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Linked notes

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