Water → HCID 19780563, compound

HRID 2081733Notes

Reaction equation

HRID 2081733 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=[O:16])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:17][N:18]=[C:19]=[S:20].[H-].[Na+].O>O1CCCC1.C(OCC)C.CCCCCC>[CH3:17][NH:18][C:19]([C:10]1([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=[O:16])=[S:20]

Participants

8

Reactant 4

HCID 962WaterHCID 11167Methyl isothiocyanateHCID 24758Sodium hydrideHCID 19780566HCID 19780566, compound

Product 1

HCID 19780563HCID 19780563, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of (±)-2-(3-nitrophenyl)cyclohexanone (1 g,4.5 mmol) and methyl isothiocyanate at 20° C. in tetrahydrofuran (15 ml) was treated with sodium hydride (120 mg, 5 mmol) added in one portion. The mixture was stirred vigorously. After 13 minutes, water (20 ml) was added and the mixture extracted with ethyl acetate (2×20ml). The combined organic extracts were dried over magnesium sulphate. Concentration in vacuo (30° C., 14 mmHg) afforded a crude oil (0.95 g) which was purified by flash chromatography over silica gel, eluting with toluene/acetone: 96/4 and trituration with equal portions of hexane and diethyl ether to give (±)-N-methyl-2-oxo-1-(3-nitrophenyl)-cyclohexanecarbothioamide (0.1 g, 0.35mmol) m.p. 128°-132° C.

Workup

  1. additionadded in one portion
  2. extractionthe mixture extracted with ethyl acetate (2×20ml)
  3. dry with materialThe combined organic extracts were dried over magnesium sulphate
  4. concentrationConcentration in vacuo (30° C., 14 mmHg)
  5. customafforded a crude oil (0.95 g) which
  6. customwas purified by flash chromatography over silica gel
  7. washeluting with toluene/acetone

Sources & evidence

ORD record
ord-8c477c5c39da4ef9b4c6f4a0847b2279
Source dataset
uspto-grants-1993_02
Patent number
US05185375

Reaction notes

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