Allylamine → HCID 2832220, compound

HRID 1268417Notes

Reaction equation

HRID 1268417 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[N+:5]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](Cl)=[O:12])([O-:7])=[O:6]>C(OCC)(=O)C>[CH2:1]([NH:4][C:11](=[O:12])[C:10]1[CH:14]=[CH:15][CH:16]=[C:8]([N+:5]([O-:7])=[O:6])[CH:9]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 7853AllylamineHCID 8495Benzoyl chloride, 3-nitro-

Product 1

HCID 2832220HCID 2832220, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

Step 1′ A 3-L, three-necked, round-bottomed flask equipped with a mechanical stirrer, a nitrogen inlet adapter, and a 500-mL pressure-equalizing addition finnel fitted with a glass stopper was purged with nitrogen. The flask was charged with allylamine (K) 33.9 g (0.593 mol), 50 mL of ethyl acetate, triethylaamine 60.0 g (0.593 mol), and then cooled with an ice-water bath. The addition funnel was charged with 3-nitro-benzoyl chloride (J) 100.0 g (0.539 mol) and 230 mL ethyl acetate, and this solution was then added dropwise to the reaction mixture over 1 h while the reaction mixture was maintained at 0° C. The reaction mixture was stirred at 0° C. for 3 h and then filtered. The filtrate was transferred to a separatory finnel and washed with 150 mL of a 10% (by volume) HCl aqueous solution, 100 mL of saturated sodium chloride solution, dried over magnesium sulfate, and the solvent volume was reduced to one-third the original volume under reduced pressure. The clear solution was cooled to 0° C. overnight. The resulting yellow solid was collected by filtration and dried in a vacuum oven at 50° C. for 6 h to afford 89.4 g (80% yield) of N-allyl-3-nitrobenzamide (L) as a yellow solid.

Workup

  1. additiona 500-mL pressure-equalizing addition finnel
  2. customfitted with a glass stopper
  3. customwas purged with nitrogen
  4. temperaturecooled with an ice-water bath
  5. additionthis solution was then added dropwise to the reaction mixture over 1 h while the reaction mixture
  6. filtrationfiltered
  7. washwashed with 150 mL of a 10% (by volume) HCl aqueous solution, 100 mL of saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. temperatureThe clear solution was cooled to 0° C. overnight
  10. filtrationThe resulting yellow solid was collected by filtration
  11. customdried in a vacuum oven at 50° C. for 6 h

Sources & evidence

ORD record
ord-e5396576fc974872bacadd0de9827f66
Source dataset
uspto-grants-2003_04
Patent number
US06555711B1

Reaction notes

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