4-Nitrobenzyl chloride → HCID 15512294, compound

HRID 1835434Notes

Reaction equation

HRID 1835434 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-707c2b7e2ff34ce79f4f57aeb65c5429
Source dataset
uspto-grants-2004_08
Patent number
US06770669B1

Reaction notes

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