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Acetic Acid → 1-Nitro-2-phenylethane

HRID 424295
Notes
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Reaction equation

HRID 424295 reaction equation
C(O)(=O)C.C(N(CC1C=CC=CC=1)CCN)C1C=CC=CC=1.[N+:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]CCCCCCCCCC)([O-:25])=[O:24].C=O>C(O)C.C(OCC)(=O)C>[N+:23]([CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)([O-:25])=[O:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 6394114N1,N1-Dibenzylethane-1,2-diamineHCID 115439441-Nitrooctadecane

Product 1

HCID 802081-Nitro-2-phenylethane

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
60 °C

Procedure

Acetic acid (1.5 mL) was added to a solution of N,N-dibenzylethylene diamine (3.0 g, 12.5 mmol) in ethanol (25 mL) and the solution was stirred at 60° C. for 10 min A white solid formed which dissolved on heating to 80° C. Compound 3 (1.73 g, 6.25 mmol) was added and the stirring was continued at 80° C. for an additional 10 min. Paraformaldehyde (2.5. g, 88 mmol) was added to this solution in small portions over a period of 30 min and the suspension was stirred for 5 h at 80° C. Solvents were removed and the residue was treated with water. The pasty solid obtained was dissolved in ethyl acetate, washed with water and dried (Na2SO4). The oil obtained was purified by silica gel chromatography. (hexane/ethyl acetate, 9/1, 7/3). UV visible fractions were collected and evaporated to give 4 as an oil. Yield: 3.2 g (64%).

Workup

  1. customformed which
  2. dissolutiondissolved
  3. temperatureon heating to 80° C
  4. waitthe stirring was continued at 80° C. for an additional 10 min
  5. stirringthe suspension was stirred for 5 h at 80° C
  6. customSolvents were removed
  7. additionthe residue was treated with water
  8. customThe pasty solid obtained
  9. washwashed with water
  10. dry with materialdried (Na2SO4)
  11. customThe oil obtained
  12. customwas purified by silica gel chromatography
  13. customUV visible fractions were collected
  14. customevaporated

Sources & evidence

ORD record
ord-610aa24dd232441789359085d983577f
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08105567B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes