1,4-dithian-2-one → HCID 21224734, compound

HRID 1584537Notes

Reaction equation

HRID 1584537 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:15])[CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[N+:12]([O-:14])=[O:13].[O:16]=[C:17]1[CH2:22][S:21][CH2:20][CH2:19][S:18]1>CO.CC(C)=O>[SH:18][CH2:19][CH2:20][S:21][CH2:22][C:17]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:15])[CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[N+:12]([O-:14])=[O:13])=[O:16]

Participants

5

Reactant 2

HCID 5427241,4-dithian-2-oneHCID 19593917HCID 19593917, compound

Product 1

HCID 21224734HCID 21224734, compoundYield 37.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

N-(2-Aminoethyl)-(2-nitroimidazol-1-yl)acetamide (40 mg, 0.23 mmol) in methanol (0.5 cm3) was added to 2-oxo-1,4-dithiane (40 mg, 0.27 mmol) in acetone (0.2 cm3) under an atmosphere of dry nitrogen. The mixture was left at room temperature and monitored by n.m.r. spectroscopy until the reaction was complete. The bulk of the solvent was removed, and the resulting material purified by reverse phase h.p.l.c. using aqueous methanol as the eluant. The pure N-{2-[(2-mercaptoethylthio)acetylamino]ethyl}-(2-nitroimidazol-1-yl)acetamide (30 mg) was isolated as a pale yellow solid.

Workup

  1. waitThe mixture was left at room temperature
  2. customThe bulk of the solvent was removed
  3. customthe resulting material purified by reverse phase h.p.l.c

Sources & evidence

ORD record
ord-bf984e4dbaa842449e4c033bcc94865f
Source dataset
uspto-grants-1999_08
Patent number
US05932707

Reaction notes

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