Diethanolamine → SR 2555

HRID 1757950Notes

Reaction equation

HRID 1757950 reaction equation
[N+:1]([C:4]1[N:5]([CH2:9][C:10]([O:12]C)=O)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[NH:14]([CH2:18][CH2:19][OH:20])[CH2:15][CH2:16][OH:17]>CO>[OH:17][CH2:16][CH2:15][N:14]([CH2:18][CH2:19][OH:20])[C:10](=[O:12])[CH2:9][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 8113DiethanolamineHCID 89851Methyl 2-nitroimidazole-1-acetate

Product 1

HCID 92390SR 2555Yield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4.00 g (21.6 mmol) of methyl 2-nitroimidazole-1-acetate and 4.0 g (38.0 mmol) of diethanolamine in 60.0 ml of methanol was stirred four days at room temperature. After removing the excess diethanolamine, the product was dissolved in 10 ml of methanol and chromatographed through a column of silica gel (70-230 mesh). Elution with 10% methanol in methylene chloride afforded 5.38 g (96%) of product as a hard gum that crystallized after several days to a cream colored hygroscopic solid on silica gel with 20% methanol in methylene chloride (Rf 0.47) and analyzed correctly for C9H14N4O5. The solubility of SR-2555 in 0.9% saline solution was over 300 mg/ml.

Workup

  1. customAfter removing the excess diethanolamine
  2. dissolutionthe product was dissolved in 10 ml of methanol
  3. customchromatographed through a column of silica gel (70-230 mesh)
  4. washElution with 10% methanol in methylene chloride

Sources & evidence

ORD record
ord-1f1c52876d0c4399a40e7803483d7e82
Source dataset
uspto-grants-1983_02
Patent number
US04371540

Reaction notes

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