Hydrochloric Acid → 1-((2-chlorothiazol-5-yl)methyl)-9-nitro-2,3,5,6,7,8-hexahydro-1H-5,8-epoxyimidazo[1,2-a]azepine

HRID 1043521Notes

Reaction equation

HRID 1043521 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]2[CH2:12][CH2:11][NH:10][C:9]2=[CH:13][N+:14]([O-:16])=[O:15])=[CH:5][N:6]=1.[CH:17](=[O:22])[CH2:18][CH2:19][CH:20]=O.Cl>C(#N)C>[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]2[C:9]3=[C:13]([N+:14]([O-:16])=[O:15])[CH:20]4[O:22][CH:17]([N:10]3[CH2:11][CH2:12]2)[CH2:18][CH2:19]4)=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12524ButanedialHCID 1845972-Chloro-5-((2-(nitromethylene)-1-imidazolidinyl)methyl)thiazole

Product 1

HCID 584962571-((2-chlorothiazol-5-yl)methyl)-9-nitro-2,3,5,6,7,8-hexahydro-1H-5,8-epoxyimidazo[1,2-a]azepineYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 50 ml round bottom flask was added 1.30 g (0.005 mol) 1-((2-chlorothiazol-5-yl)methyl)-2-(nitromethylene)imidazolidine, 30 ml dry acetonitrile, 0.860 g (0.01 mol) succinaldehyde and catalytic concentrated HCl. The reaction was stirred at r.t. and monitored by TLC. After completion, the mixture was evaporated to remove solvent and purified by column chromatography to afford final product as faint yellow powder with 63% yield.

Workup

  1. customAfter completion, the mixture was evaporated
  2. customto remove solvent
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-3aacaae674ad447083b75dfccc4eb126
Source dataset
uspto-grants-2013_10
Patent number
US08563546B2

Reaction notes

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