Lithium Bromide → HCID 11283100, compound

HRID 503673Notes

Reaction equation

HRID 503673 reaction equation
CS(O[CH2:6][CH2:7][N:8]([CH2:27][CH2:28]OS(C)(=O)=O)[C:9]1[CH:14]=[C:13]([C:15]([NH:17][CH2:18][CH2:19][OH:20])=[O:16])[C:12]([N+:21]([O-:23])=[O:22])=[CH:11][C:10]=1[N+:24]([O-:26])=[O:25])(=O)=O.[Li+].[Br-:35].[Na+].[Br-:37]>CN(C=O)C>[Br:35][CH2:6][CH2:7][N:8]([CH2:27][CH2:28][Br:37])[C:9]1[C:10]([N+:24]([O-:26])=[O:25])=[CH:11][C:12]([N+:21]([O-:23])=[O:22])=[C:13]([CH:14]=1)[C:15]([NH:17][CH2:18][CH2:19][OH:20])=[O:16]

Participants

5

Reactant 3

HCID 82050Lithium BromideHCID 253881Sodium BromideHCID 16115123HCID 16115123, compound

Product 1

HCID 11283100HCID 11283100, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 9a (1.80 g, 3.50 mmol) and LiBr (0.43 g, 4.95 mmol) in DMF (5 mL) was stirred at 60° C. for 2 h. The reaction was then poured into saturated NaBr solution and extracted with EtOAc (2×). The combined extracts were washed with saturated NaBr solution, dried (Na2SO4) and concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with EtOAc, to give 5-[bis(2-bromoethyl)amino]-N-(2-hydroxyethyl)-2,4-dinitrobenzamide (10a) (0.78 g, 46%):

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined extracts were washed with saturated NaBr solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. washeluting with EtOAc

Sources & evidence

ORD record
ord-8c3458a867a0443dbe629774c42717e9
Source dataset
uspto-grants-2010_08
Patent number
US07776924B2

Reaction notes

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