Dimethylformamide → N-Benzylnormechlorethamine

HRID 2376646Notes

Reaction equation

HRID 2376646 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][Cl:8].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN(C=O)C>C(N(CC)CC)C>[Cl:2][CH2:3][CH2:4][N:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][CH2:7][Cl:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 5928N-Benzylnormechlorethamine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

An ice bath is used to cool a mixture of 150 g of N,N-bis(2-chloroethyl)amine hydrochloride and 100 ml of benzyl bromide in 1 000 ml of DMF and then 120 ml of triethylamine are added dropwise and the mixture is left with stirring at AT overnight. The reaction mixture is concentrated under vacuum, the residue is taken up in water and extracted 3 times with ether, the organic phases are dried over Na2SO4 and the solvent is evaporated under vacuum. This gives 113 g of the expected product.

Workup

  1. customAn ice bath is used
  2. temperatureto cool
  3. waitthe mixture is left
  4. concentrationThe reaction mixture is concentrated under vacuum
  5. extractionextracted 3 times with ether
  6. dry with materialthe organic phases are dried over Na2SO4
  7. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-f7d0f4c392404cf697547849884b30bd
Source dataset
uspto-grants-2008_12
Patent number
US07468368B2

Reaction notes

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