Nitrogen mustard hydrochloride → HCID 673952, compound

HRID 1708067Notes

Reaction equation

HRID 1708067 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH2:11].Cl.Cl[CH2:14][CH2:15][N:16]([CH2:18][CH2:19]Cl)[CH3:17]>ClC1C=CC=CC=1.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[CH2:19][CH2:18][N:16]([CH3:17])[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 5935Nitrogen mustard hydrochlorideHCID 226912-Chloro-5-nitroaniline

Product 1

HCID 673952HCID 673952, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 2-chloro-5-nitrobenzenamine (7.95 g) and 2-chloro-N-(2-chloroethyl)-N-methylethanamine hydrochloride (8.86 g) in chlorobenzene (40 ml) under nitrogen was heated to reflux for 3 days before cooling and diluting with dichloromethane (60 ml). The reaction mixture was then extracted with water (2×500 ml), the aqueous layers combined and basified with 2N sodium hydroxide, then extracted with dichloromethane (4×400 ml). The combined, dried extracts were concentrated in vacuo to give a dark brown oil (7.82 g) which was purified by flash column chromatography eluting with ether to give a dark brown oil which crystallised upon standing. The material was dissolved in ethanol (40 ml) and boiled up with some charcoal (300 mg). The hot ethanolic suspension was filtered and concentrated in vacuo to give the title compound as a yellow oil which crystallised on standing (5.25 g) m.p.63°-64° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 days
  3. temperaturebefore cooling
  4. extractionThe reaction mixture was then extracted with water (2×500 ml)
  5. extractionextracted with dichloromethane (4×400 ml)
  6. customdried extracts
  7. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-1cb24627a29d4781bf6269c63fa75feb
Source dataset
uspto-grants-1994_10
Patent number
US05356893

Reaction notes

Loading…