Ammonium Chloride → HCID 11749117, compound

HRID 2111511Notes

Reaction equation

HRID 2111511 reaction equation
[CH2:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[NH2:10])=[CH:5][CH:4]=1)[CH3:2].[O:17]=[CH:18][C@@H:19]([C@H:21]([C@@H:23]([C@@H:25]([CH2:27][OH:28])[OH:26])[OH:24])[OH:22])O.[Cl-].[NH4+]>CO>[CH2:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[NH:10][C@@H:27]2[O:28][C@H:19]([CH2:18][OH:17])[C@@H:21]([OH:22])[C@H:23]([OH:24])[C@H:25]2[OH:26])=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 11572028HCID 11572028, compound

Product 1

HCID 11749117HCID 11749117, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(4-Ethylbenzyl)aniline 1 (500 mg) was dissolved in methanol (5 ml), and thereto are added D-(+)-glucose 2 (516 mg) and ammonium chloride (25 mg), and the mixture was heated under reflux for 2 hours. Methanol was evaporated under reduced pressure, and water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (chloroform:methanol=40:1-20:1) to give the desired 2-(4-ethylbenzyl)-N-(β-D-glucopyranosyl)aniline 3 (495 mg) as colorless crystals. APCI-Mass m/Z 374 (M+H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customMethanol was evaporated under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customthe solvent was evaporated
  9. customThe residue was purified by silica gel column chromatography (chloroform:methanol=40:1-20:1)

Sources & evidence

ORD record
ord-74320cc61f1348ef9231a4fb4f204d96
Source dataset
uspto-grants-2009_04
Patent number
US07521430B2

Reaction notes

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