Hydrochloric Acid → N,N-Bis(2-chloroethyl)benzylamine hydrochloride

HRID 2407493Notes

Reaction equation

HRID 2407493 reaction equation
O[CH2:2][CH2:3][N:4]([CH2:12][CH2:13]O)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.S(Cl)([Cl:17])=O.[ClH:19]>[N+](C)([O-])=O>[ClH:17].[Cl:19][CH2:2][CH2:3][N:4]([CH2:12][CH2:13][Cl:17])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 75532,2'-((Phenylmethyl)imino)bisethanolHCID 24386Thionyl Chloride

Product 1

HCID 2777881N,N-Bis(2-chloroethyl)benzylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

To a solution of bis(2-hydroxyethyl)benzylamine (19.5 g 0.1 mol) in nitromethane (150 mL) cooled with a water/ice bath is added thionyl chloride (60 mL). The mixture is stirred at room temperature for 2 h, then at 80° C. for 1 h 30. After cooling again with a water/ice bath, diisopropyl oxyde (350 mL) is added, causing the hydrochloride to precipitate. This is filtrated, rinsed with diisopropyl oxide and dried to give bis(2-chloroethyl)benzylamine hydrochloride.

Workup

  1. waitat 80° C. for 1 h 30
  2. temperatureAfter cooling again with a water/ice bath
  3. additiondiisopropyl oxyde (350 mL) is added
  4. customto precipitate
  5. filtrationThis is filtrated
  6. washrinsed with diisopropyl oxide
  7. customdried

Sources & evidence

ORD record
ord-ba29e1e0b319435181be7a2af7b91a90
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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