Bis(2-chloroethyl)amine hydrochloride → N,N-bis(2chloroethyl)-N'-phenylsulphamide

HRID 413276Notes

Reaction equation

HRID 413276 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[S:5]1(=[O:16])=[O:15].Cl.[Cl:18]CCNCCCl>C1(C)C(C)=CC=CC=1>[Cl:1][CH2:2][CH2:3][N:4]([CH2:8][CH2:7][Cl:18])[S:5]([NH:6][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 223908502-(2-Chloroethyl)-5-phenyl-1,2,5-thiadiazolidine-1,1-dioxide

Product 1

HCID 22390755N,N-bis(2chloroethyl)-N'-phenylsulphamide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
100 °C

Procedure

66 g of the product obtained in Step 1 above are added to a suspension of 38.6 g of N,N-bis(2-chloroethyl)amine hydrochloride in 265 ml of xylene heated to 100° C. The reaction mixture is heated at 140° C. for 12 hours and, after cooling, filtered over a frit. The filtrate is concentrated and then purified by flash chromatography (eluant CH2Cl2/AcOEt: 95/5) to yield the expected product.

Workup

  1. temperatureThe reaction mixture is heated at 140° C. for 12 hours
  2. temperatureafter cooling
  3. filtrationfiltered over a frit
  4. concentrationThe filtrate is concentrated
  5. custompurified by flash chromatography (eluant CH2Cl2/AcOEt: 95/5)

Sources & evidence

ORD record
ord-1d5c6a4690ba4ac9a3d0f4173cf4b2d9
Source dataset
uspto-grants-2003_05
Patent number
US06566364B2

Reaction notes

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