Benzoyl chloride → Methyl 4-(2-benzenecarbonylamino-ethoxy)benzoate

HRID 29697Notes

Reaction equation

HRID 29697 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[C:17]1([C:16]([NH:2][CH2:3][CH2:4][O:5][C:6]2[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=2)=[O:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 50988568Methyl 4-(2-aminoethoxy)benzoate hydrochloride

Product 1

HCID 14426627Methyl 4-(2-benzenecarbonylamino-ethoxy)benzoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of methyl 4-(2-amino-ethoxy)benzoate hydrochloride (0.232 g, 1 mmol) in THF (6 ml) was added benzoyl chloride (0.140 g, 1 mmol) followed by triethylamine (0.121 g, 1.2 mmol). The reaction mixture was stirred for 1 h and then diluted with ethyl acetate. The organic layer was washed with 0.5 M aqueous HCl, saturated sodium bicarbonate solution, and brine. The organic layer was concentrated in vacuo to give methyl 4-(2-benzenecarbonylamino-ethoxy)benzoate which was directly used in the next step.

Workup

  1. washThe organic layer was washed with 0.5 M aqueous HCl, saturated sodium bicarbonate solution, and brine
  2. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-f7e74a8e7fba43faafa0ea478990918e
Source dataset
uspto-grants-2008_09
Patent number
US07420089B2

Reaction notes

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