Lithium Bromide → 5-[(2-bromoethyl)(2-chloroethyl)amino]-2,4-dinitrobenzamide

HRID 503669Notes

Reaction equation

HRID 503669 reaction equation
CS(O[CH2:6][CH2:7][N:8]([CH2:24][CH2:25][Cl:26])[C:9]1[CH:14]=[C:13]([C:15]([NH2:17])=[O:16])[C:12]([N+:18]([O-:20])=[O:19])=[CH:11][C:10]=1[N+:21]([O-:23])=[O:22])(=O)=O.[Li+].[Br-:28]>CC#N>[Br:28][CH2:6][CH2:7][N:8]([CH2:24][CH2:25][Cl:26])[C:9]1[C:10]([N+:21]([O-:23])=[O:22])=[CH:11][C:12]([N+:18]([O-:20])=[O:19])=[C:13]([CH:14]=1)[C:15]([NH2:17])=[O:16]

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 378686HCID 378686, compound

Product 1

HCID 100236185-[(2-bromoethyl)(2-chloroethyl)amino]-2,4-dinitrobenzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-[5-(aminocarbonyl)(2-chloroethyl)-2,4-dinitroanilino]ethyl methanesulfonate (5) [Friedlos et al., J. Med. Chem. 1997, 40, 1270] (0.91 g, 2.2 mmol) and LiBr (0.21 g, 2.4 mmol) in anhydrous MeCN (25 mL) was stirred under reflux for 1.5 h, then concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with CH2Cl2/EtOAc (3:2) to give a crude product contaminated with the corresponding dibromo mustard. Purification by multiple recrystallisations from EtOAc/I—Pr2O gave IIa2 (595 mg, 68%):

Workup

  1. temperatureunder reflux for 1.5 h
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was chromatographed on silica gel
  4. washeluting with CH2Cl2/EtOAc (3:2)

Sources & evidence

ORD record
ord-5256ddf84e22406c87cc73f1b8df9b0a
Source dataset
uspto-grants-2010_08
Patent number
US07776924B2

Reaction notes

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