Methanol → 4-(4-Oxo-2-thioxo-1-(4-methylphenyl)-1,3-diazaspiro[4.5]dec-3-yl)-2-trifluoromethylbenzonitrile

HRID 2233683Notes

Reaction equation

HRID 2233683 reaction equation
N=[C:2]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[N:5]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:4](=[S:19])[N:3]1[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:21]=1.C[OH:33].O>Cl>[O:33]=[C:2]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[N:5]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:4](=[S:19])[N:3]1[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 866098544-(4-Imino-2-thioxo-1-(4-methylphenyl)-1,3-diazaspiro[4.5]dec-3-yl)-2-trifluoromethylbenzonitrile

Product 1

HCID 159517224-(4-Oxo-2-thioxo-1-(4-methylphenyl)-1,3-diazaspiro[4.5]dec-3-yl)-2-trifluoromethylbenzonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 9b (0.035 g, 0.08 mmol) in HCl aq., 2N (1 ml) and methanol (3 ml) was heated to reflux for 2 h. After being cooled to room temperature, the reaction mixture was poured into cold water (5 ml) and extracted with ethyl acetate (6 ml). The organic layer was dried over MgSO4, concentrated and chromatographed (dichloromethane) to yield 4-(4-Oxo-2-thioxo-1-(4 -methylphenyl)-1,3-diazaspiro[4.5]dec-3-yl)-2-trifluoromethylbenzonitrile, 9c, [RD48](0.034 g, 0.076 mmol, 95%) as a white powder.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. extractionextracted with ethyl acetate (6 ml)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customchromatographed (dichloromethane)

Sources & evidence

ORD record
ord-b60948086b404e1fbad5681eecad2dc7
Source dataset
uspto-grants-2010_05
Patent number
US07709517B2

Reaction notes

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