Hydrochloric Acid → HCID 178526717, compound

HRID 1158309Notes

Reaction equation

HRID 1158309 reaction equation
O1CCCC1.C(CC[N:10]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][N:12]=[C:11]1[S:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)#N.Cl.O>C(OCC)(=O)C>[N+:15]([C:14]1[N:10]=[C:11]([S:18][C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)[NH:12][CH:13]=1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 230802591-(2-Cyanoethyl)-5-nitro-2-(4-nitrophenylthio)imidazole

Product 1

HCID 178526717HCID 178526717, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To tetrahydrofuran (1 ml) solution of 1-(2-cyanoethyl)-5-nitro-2-(4-nitrophenylthio)imidazole (36 mg) was added 1,8-diazabicyclo[5.4.0]undecene-7 (0.02 ml) at a room temperature, and stirred at the same temperature for 5 hours. To the reaction mixture were added 1N hydrochloric acid (0.2 ml), water and ethyl acetate, then the organic layer was taken by liquid separation. The ethyl acetate layer was washed with water and an aqueous solution being saturated with sodium chloride, then dried over anhydrous sodium sulfate. The residue obtained by removal of the solvent by distillation was purified by use of a silica gel column chromatography (eluent: dichloromethane/ethyl acetate=4/1), there was obtained 4-nitro-2-(4-nitrophenylthio)imidazole (27 mg, yield 91%) as pale yellow powder product.

Workup

  1. customthe organic layer was taken by liquid separation
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained by removal of the solvent by distillation
  5. customwas purified by use of a silica gel column chromatography (eluent: dichloromethane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-e81efad746774b3398306ea3556219df
Source dataset
uspto-grants-2010_10
Patent number
US07807843B2

Reaction notes

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