Sodium Iodide → N-[3,5-bis[(decylamino)carbonyl]phenyl]glycine methyl ester

HRID 1110220Notes

Reaction equation

HRID 1110220 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:22])[CH:5]=[C:6]([C:8]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:9])[CH:7]=1.Br[CH2:35][C:36]([O:38][CH3:39])=[O:37].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O.CN(C=O)C.O>[CH3:39][O:38][C:36](=[O:37])[CH2:35][NH:1][C:2]1[CH:3]=[C:4]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:22])[CH:5]=[C:6]([C:8]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:9])[CH:7]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 193889485-amino-N,N'-didecyl-1,3-benzenedicarboxamide

Product 1

HCID 19388947N-[3,5-bis[(decylamino)carbonyl]phenyl]glycine methyl esterYield 67%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.202 g (0.455 mmol) of 5-amino-N,N'-didecyl-1,3-benzenedicarboxamide, 0.17 ml (1.8 mmol) of methyl bromoacetate, 0.14 g (1 mmol) of potassium carbonate and 0.15 g (1 mmol) of sodium iodide in 10 ml of acetone and 2 ml of DMF was stirred at reflux for 20 hours. Water was added and the product was extracted with ethyl acetate. The dried extract was concentrated at reduced pressure to an oil which was crystallized from methanol-water to give 0.1608 g (67% yield, mp 108°-109°) of N-[3,5-bis[(decylamino)carbonyl]phenyl]glycine methyl ester.

Workup

  1. temperatureat reflux for 20 hours
  2. extractionthe product was extracted with ethyl acetate
  3. extractionThe dried extract
  4. concentrationwas concentrated at reduced pressure to an oil which
  5. customwas crystallized from methanol-water

Sources & evidence

ORD record
ord-9b57ccfd78a3481f9e2b732f240eee33
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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