Methyl isothiocyanate → HCID 19973438, compound

HRID 1440249Notes

Reaction equation

HRID 1440249 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][N:7]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:15])[CH:8]=1)([O-:3])=[O:2].CC(C)([O-])C.[K+].[CH3:22][N:23]=[C:24]=[S:25].[Cl-].[NH4+]>O1CCCC1.CN(C)C=O.O>[CH3:22][NH:23][C:24]([C:9]1([N:7]2[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[CH:6]2)[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[O:15])=[S:25]

Participants

8

Reactant 4

HCID 11167Methyl isothiocyanateHCID 25517Ammonium ChlorideHCID 15341318HCID 15341318, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19973438HCID 19973438, compoundYield 45.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen atmosphere, a suspension of 76.40 g (0.365 mol) of the 2-(4-nitroimidazol-1-yl)cyclohexanone prepared in the Preparative Example 10 in 1.2 l of tetrahydrofuran was cooled with ice, followed by the addition of 45.16 g (0.402 mol) of potassium t-butoxide. The obtained reddish-purple reaction mixture was stirred under cooling with ice for one hour, followed by the addition of a solution of 27.5 ml (0.402 mol) of methyl isothiocyanate in 100 ml of tetrahydrofuran and 300 ml of dimethylformamide in this order. The reaction mixture was stirred for one hour, while the temperature thereof was raised to room one. A saturated aqueous solution of ammonium chloride and water were added to the resulting mixture successively, followed by the extraction with chloroform. The organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate, and concentrated in a vacuum. The residue was triturated with chloroform to give 46.98 g of the title compound as a light-brown powder. The mother liquor was concentrated in a vacuum and the residue was triturated with chloroform again to give 9.97 g of the title compound as a light-brown powder. Further, the mother liquor was concentrated in a vacuum and the residue was triturated with ethyl acetate to give 3.24 g of the title compound as a brown powder. Thus, 60.14 g of the title compound was obtained in total (yield: 58%).

Workup

  1. temperaturewas cooled with ice
  2. temperatureunder cooling with ice for one hour
  3. stirringThe reaction mixture was stirred for one hour, while the temperature
  4. temperaturethereof was raised to room one
  5. extractionfollowed by the extraction with chloroform
  6. washThe organic phase was washed with a saturated aqueous solution of common salt
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in a vacuum
  9. customThe residue was triturated with chloroform

Sources & evidence

ORD record
ord-9ecacc91cc694a528f06fcf86145ab0f
Source dataset
uspto-grants-1996_03
Patent number
US05498634

Reaction notes

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