Water → N-Benzylnormechlorethamine

HRID 895639Notes

Reaction equation

HRID 895639 reaction equation
O[CH2:2][CH2:3][N:4]([CH2:12]CO)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.S(Cl)([Cl:17])=O.O.C(=O)([O-])O.[Na+].Cl[CH2:26][Cl:27]>>[Cl:17][CH2:2][CH2:3][N:4]([CH2:12][CH2:26][Cl:27])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 75532,2'-((Phenylmethyl)imino)bisethanolHCID 24386Thionyl ChlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 5928N-Benzylnormechlorethamine

Procedure

Bis(2-hydroxyethyl)benzylamine (1 g) was dissolved in dichloromethane (20 ml), added with thionyl chloride (1.9 ml) with ice cooling and stirred at room temperature for 2.5 hours. The reaction mixture was added with water (10 ml) with ice cooling, and adjusted to pH 7 with saturated aqueous sodium hydrogencarbonate. The layers were separated and the aqueous layer was further extracted with dichloromethane (20 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to obtain bis(2-chloroethyl)benzylamine (1.090 g).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was further extracted with dichloromethane (20 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cc7f206edcb146ceb7adb046a4fa0f9b
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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