Nitrogen mustard hydrochloride → HCID 18958756, compound

HRID 1708068Notes

Reaction equation

HRID 1708068 reaction equation
[F: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.CO>[F: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 677852-Fluoro-5-nitroaniline

Product 1

HCID 18958756HCID 18958756, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 2-fluoro-5-nitrobenzenamine (4.06 g) and 2-chloro-N-(2-chloroethyl)-N-methylethanamine hydrochloride (5.006 g) in chlorobenzene (20 ml) was heated at reflux under nitrogen for 21/2 days. The dark solid was dissolved in methanol (150 ml) and the solution was then concentrated in vacuo onto silica and purified by FCC eluting with System A (400:8:1) to give impure material (1.9 g). This was purified again by FCC eluting with System A (300:8:1) to give the title compound as a crystalline brown solid (360 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 21/2 days
  3. concentrationthe solution was then concentrated in vacuo onto silica
  4. custompurified by FCC
  5. washeluting with System A (400:8:1)

Sources & evidence

ORD record
ord-97f5a43ea1cf4e61a3b50ddc7c3f2f14
Source dataset
uspto-grants-1994_10
Patent number
US05356893

Reaction notes

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