4-Nitrobenzyl chloride → HCID 15512294, compound

HRID 1744872Notes

Reaction equation

HRID 1744872 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][NH:13][CH2:14][C:15]#[CH:16]>ClCCl.C(N(CC)CC)C>[CH3:12][N:13]([CH2:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH2:14][C:15]#[CH:16]

Participants

5

Reactant 2

HCID 74824-Nitrobenzyl chlorideHCID 96160N-methylpropyn-2-ylamine

Product 1

HCID 15512294HCID 15512294, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

3.72 g (22.0 mmol) of p-nitrobenzyl chloride in 20 ml of dichloromethane is added, dropwise, at 0° C. to a solution of 1 g (1.45 mmol) of N-methylpropargylamine in 15 ml of dichloromethane and 3.1 ml of triethylamine. After stirring overnight, the reaction mixture is concentrated to dryness under vacuum, and the residue is diluted with dichloromethane and 40 ml of a saturated solution of NaCl. After stirring and decanting, the organic phase is separated and dried over magnesium sulphate, filtered and concentrated under vacuum. The expected product is obtained after chromatography on a silica column, eluent: (20% ethyl acetate in heptane), the pure fractions, after evaporation, produce a brown solid with a yield of 80%. Melting point: 47–49° C.

Workup

  1. customat 0° C.
  2. concentrationthe reaction mixture is concentrated to dryness under vacuum
  3. additionthe residue is diluted with dichloromethane and 40 ml of a saturated solution of NaCl
  4. stirringAfter stirring
  5. customdecanting
  6. customthe organic phase is separated
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b25e54b52a734a9e8f6cae0e854b6921
Source dataset
uspto-grants-2006_03
Patent number
US07019025B2

Reaction notes

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