Oxalyl chloride → Ethyl 6-[o-[p-(4-phenylbutoxy)benzamido]phenyl]hexanate

HRID 847283Notes

Reaction equation

HRID 847283 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(CCCCOC2C=CC(C(O)=O)=CC=2)C=CC=CC=1.C(Cl)(=O)C(Cl)=O.[NH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][C:59]([O:61][CH2:62][CH3:63])=[O:60]>C(Cl)Cl.N1C=CC=CC=1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=3[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][C:59]([O:61][CH2:62][CH3:63])=[O:60])=[O:17])=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 110438254-(4-Phenylbutoxy)benzoic AcidHCID 11055348Benzoyl chloride, 4-(4-phenylbutoxy)-HCID 19882678Ethyl 6-(o-aminophenyl)hexanate

Product 1

HCID 19882682Ethyl 6-[o-[p-(4-phenylbutoxy)benzamido]phenyl]hexanate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of p-(4-phenylbutoxy)benzoyl chloride prepared from 1 g of p-(phenylbutoxy)benzoic acid and 2 ml of oxalyl chloride in methylene chloride was added to a solution of 0.6 g of ethyl 6-(o-aminophenyl)hexanate obtained in Reference Example 17 in 10 ml of pyridine at temperature less than -30° C. The mixture was stirred at room temperature overnight and concentrated under reduced pressure. Toluene was added to the residue. The mixture was washed with diluted hydrochloric acid and then with water and dried over anhydrous magnesium sulfate. The systems was concentrated under reduced pressure to obtain 1.0 g of oily ethyl 6-[o-[p-(4-phenylbutoxy)benzamido]phenyl]hexanate.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionToluene was added to the residue
  3. washThe mixture was washed with diluted hydrochloric acid
  4. dry with materialwith water and dried over anhydrous magnesium sulfate
  5. concentrationThe systems was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5f149379a3b8410086e921a77f6fce17
Source dataset
uspto-grants-1992_08
Patent number
US05140046

Reaction notes

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