Hydrochloric Acid → HCID 67050115, compound

HRID 2103927Notes

Reaction equation

HRID 2103927 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].N1C=CN=C1.[C:20]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])([CH3:22])[CH3:21].[Cl-].[NH4+].Cl>CN(C)C=O>[Si:24]([O:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:26])[CH3:25]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 15018924-Hydroxymethyl-3-nitrobenzoic acid

Product 1

HCID 67050115HCID 67050115, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxymethyl-3-nitrobenzoic acid (1.50 g, 7.62 mmol) and imidazole (1.55 g, 22.8 mmol) in dimethylformamide (20 mL) was added tert-butyldimethyl-silyl chloride (2.23 g, 14.8 mmol), and then the reaction mixture was stirred at room temperature for 15 hours. To the reaction mixture, saturated ammonium chloride aqueous solution was added and acidified with 1 M hydrochloric acid. The aqueous layer was extracted with ethyl acetate three times. The combined organic layer was washed with saturated ammonium chloride aqueous solution, water and brine, dried with sodium sulfate, filtered, and concentrated under the reduced pressure. The residue was purified by silica gel column chromatography to give the desired product as a white solid (1.73 g, yield 73%).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate three times
  2. washThe combined organic layer was washed with saturated ammonium chloride aqueous solution, water and brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under the reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e0a6ddfee96e4652a26bbccf06a412f0
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

Loading…