Nitrogen mustard hydrochloride → HCID 673952, compound

HRID 1708383Notes

Reaction equation

HRID 1708383 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 FCC eluting with ether to give a dark brown oil which crystallised upon standing. This material was dissolved in ethanol (40 ml) and boiled up with some charcoal (300 mg). The hot ethanolic suspension was filtered through a pad of hyflo 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-17d8dd56a903443dbcd1936c1ec559da
Source dataset
uspto-grants-1994_10
Patent number
US05358948

Reaction notes

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