Benzylamine → HCID 67318859, compound

HRID 1373484Notes

Reaction equation

HRID 1373484 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([NH:7][S:8]([CH2:11][C:12](O)=O)(=[O:10])=[O:9])=[CH:5][C:4]=1[N+:17]([O-:19])=[O:18].[CH3:20][O:21][C:22]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:32][CH3:33])[C:23]=1C=O.C(N)C1C=CC=CC=1.C(OCC)(=O)C>C(O)(=O)C>[CH3:31][O:30][C:28]1[CH:27]=[C:26]([O:32][CH3:33])[CH:23]=[C:22]([O:21][CH3:20])[C:29]=1[CH:12]=[CH:11][S:8]([NH:7][C:6]1[CH:15]=[CH:16][C:3]([O:2][CH3:1])=[C:4]([N+:17]([O-:19])=[O:18])[CH:5]=1)(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8857Ethyl AcetateHCID 700192,4,6-TrimethoxybenzaldehydeHCID 467053353-Nitro-4-methoxyanilinosulfonyl acetic acid

Product 1

HCID 67318859HCID 67318859, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-methoxy-3-nitroanilinesulfonylacetic acid (10 mmol) and 2,4,6-trimethoxy-benzaldehyde (10 mmol) in glacial acetic acid (15 mL) was stirred at room temperature for 10 min. A catalytic amount of benzylamine (300 microliters) was added to the solution. The solution was then refluxed for 8 h. The reaction mixture was then cooled to room temperature. To the cooled reaction mixture was added ethyl acetate. A solid precipitate formed and was separated by filtration. Additional of ethyl acetate (30 mL) was added and the resulting mixture was washed sequentially with saturated sodium bicarbonate, dilute HCL and brine. The organic layer was dried over anhydrous sodium sulfate and then concentrated under vacuum. The solid residue obtained was recrystallized from 2-propanol. (m.p 177–179° C.; yield 48–52%).

Workup

  1. temperatureThe solution was then refluxed for 8 h
  2. customTo the cooled reaction mixture
  3. customA solid precipitate formed
  4. customwas separated by filtration
  5. additionAdditional of ethyl acetate (30 mL) was added
  6. washthe resulting mixture was washed sequentially with saturated sodium bicarbonate
  7. additiondilute HCL and brine
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe solid residue obtained
  11. customwas recrystallized from 2-propanol
  12. custom(m.p 177–179° C.; yield 48–52%)

Sources & evidence

ORD record
ord-1b39dface95644cdb49a808b2a7dbd97
Source dataset
uspto-grants-2007_01
Patent number
US07161031B2

Reaction notes

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