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

HRID 612321Notes

Reaction equation

HRID 612321 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-e8ca9205bba34ba8bcf423dda68c4f27
Source dataset
uspto-grants-1999_12
Patent number
US06004531

Reaction notes

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