2-Nitrobenzyl chloride → HCID 70359167, compound

HRID 1633183Notes

Reaction equation

HRID 1633183 reaction equation
[CH2:1]([NH2:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[N+:20]([C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25]Cl)([O-:22])=[O:21]>C(O)C>[N+:20]([C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][NH2:19])([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 119212-Nitrobenzyl chlorideHCID 15793Octadecylamine

Product 1

HCID 70359167HCID 70359167, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Octadecylamine (13.5 g, 0.05 mol) was dissolved in warm absolute ethanol (300 ml) and 2-nitrobenzyl chloride was added. After three days at room temperature, the mixture was cooled and the unreacted octadecylamine which crystallized was removed by filtration. The filtrate was evaporated to dryness and the residue dissolved in dilute aqueous hydrochloric acid. Ether extraction of the acidic solution removed unreacted 2-nitrobenzyl chloride. The aqueous layer was made basic with potassium hydroxide solution and the resulting mixture was extracted with ether. The dried ether layer was evaporated to yield an oil which crystallized. Crystallization from methanol gave pure product (0.8 g, m.p. 53°-56° C.).

Workup

  1. temperaturethe mixture was cooled
  2. customthe unreacted octadecylamine which crystallized
  3. customwas removed by filtration
  4. customThe filtrate was evaporated to dryness
  5. dissolutionthe residue dissolved in dilute aqueous hydrochloric acid
  6. extractionEther extraction of the acidic solution
  7. customremoved unreacted 2-nitrobenzyl chloride
  8. extractionthe resulting mixture was extracted with ether
  9. customThe dried ether layer was evaporated
  10. customto yield an oil which
  11. customcrystallized
  12. customCrystallization from methanol

Sources & evidence

ORD record
ord-5a9392ef616447bbbc06ba1d24ff8c41
Source dataset
uspto-grants-1984_10
Patent number
US04478967

Reaction notes

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