Hydrochloric Acid → HCID 67210657, compound

HRID 869531Notes

Reaction equation

HRID 869531 reaction equation
[Cl:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(N(CC)CC)C.[CH3:19][O:20][CH2:21][C:22](Cl)=[O:23].Cl>ClCCl>[Cl:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([NH:5][C:22](=[O:23])[CH2:21][O:20][CH3:19])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 1010683-Chloro-2-nitroaniline

Product 1

HCID 67210657HCID 67210657, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

[step 1] 3-Chloro-2-nitroaniline (2.0 g, 11.6 mmol) was dissolved in dichloromethane, triethylamine (2.6 mL, 18.5 mmol) and 2-methoxyacetyl chloride (1.4 mL, 15.1 mmol) were added, and the mixture was stirred at 70° C. for 18 hr. To the mixture was added 1 mol/L hydrochloric acid, and the mixture was extracted 3 times with chloroform. The combined organic layers were washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 v/v-50/50 v/v) to give N-(3-chloro-2-nitrophenyl)-2-methoxyacetamide (1.7 g, 62%).

Workup

  1. extractionthe mixture was extracted 3 times with chloroform
  2. washThe combined organic layers were washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 v/v-50/50 v/v)

Sources & evidence

ORD record
ord-4403110211a049ce95ef7ce98e75652b
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

Loading…