Iodide Ion → HCID 22013732, compound

HRID 1532681Notes

Reaction equation

HRID 1532681 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=O.[I-].[CH2:9]([NH:27][C:28]1[C:29]([NH2:34])=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)C.O.C(OCC)(=O)C>[CH2:9]([N:27]1[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[N:34]=[C:2]1[C:1]([O:5][CH2:6][CH3:7])=[O:4])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

8

Reactant 4

HCID 30165Iodide IonHCID 61475Sodium Thiosulfate PentahydrateHCID 70211Ethyl oxoacetateHCID 22013747HCID 22013747, compound

Product 1

HCID 22013732HCID 22013732, compoundYield 75.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl glyoxylate (7.861 g) and iodide (4.886 g) were added to a solution containing N-octadecyl-1,2-benzenediamine (6.940 g) in ethanol (100 ml) and the mixture was stirred for 2 hours at room temperature. A solution containing sodium thiosulfate pentahydrate (4.813 g) in water (60 ml) was added dropwise to the reaction mixture while being stirred. The reaction mixture, with ethyl acetate added thereto, was washed with saturated brine, dried over sodium sulfate anhydride, and concentrated. The residue (10.06 g) was purified by silica gel column chromatography (silica gel 255 g, chloroform), thereby yielding the entitled compound (6.442 g) as pale yellow solid.

Workup

  1. additionwas added dropwise to the reaction mixture
  2. stirringwhile being stirred
  3. washwas washed with saturated brine
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated
  6. customThe residue (10.06 g) was purified by silica gel column chromatography (silica gel 255 g, chloroform)

Sources & evidence

ORD record
ord-0ba52ffafd7c4794ae57e5f51340cd09
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

Loading…