Methylcyclohexane → HCID 178493326, compound

HRID 1254933Notes

Reaction equation

HRID 1254933 reaction equation
[CH3:1][O:2][C:3]1[C:11]([S:12]([CH3:14])=[O:13])=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[OH:19][C:20]1[N:21]([CH3:25])[N:22]=[CH:23][CH:24]=1.CC1C=NC=CC=1.S(Cl)(Cl)=O.CC1CCCCC1>C(OCC)(=O)C.O>[OH:19][C:20]1[N:21]([CH3:25])[N:22]=[CH:23][C:24]=1[C:5]([C:4]1[CH:8]=[CH:9][C:10]([C:15]([F:18])([F:17])[F:16])=[C:11]([S:12]([CH3:14])=[O:13])[C:3]=1[O:2][CH3:1])=[O:7]

Participants

8

Reactant 5

HCID 7962MethylcyclohexaneHCID 79703-MethylpyridineHCID 24386Thionyl Chloride2×HCID 679801182-Methoxy-3-methylsulfinyl-4-trifluoromethylbenzoic acidHCID 178481816HCID 178481816, compound

Product 1

HCID 178493326HCID 178493326, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.0 g of 2-methoxy-3-methylsulfinyl-4-trifluoromethylbenzoic acid and 1.02 g of 3-hydroxy-2-methylpyrazole are suspended in 20 ml of ethyl acetate and 5.07 ml of 3-methylpyridine under an inert atmosphere and cooled to −25° C. with stirring. 1.24 g of thionyl chloride are then slowly added dropwise such that the temperature always remains below −20° C. Following the complete addition of the thionyl chloride, the mixture is stirred for a further 20 minutes. 40 μl of cold water and 20 ml of methylcyclohexane are then added. The mixture is then stirred for a further 20 minutes at −25° C. The suspension is filtered and washed once with 10 ml of methylcyclohexane and twice with 10 ml of water in each case. Drying gives 3.67 g of (5-hydroxy-1-methyl-1H-pyrazol-4-yl)[2-methoxy-3-(methylsulfinyl)-4-(trifluoromethyl)phenyl]methanone (86.5% yield).

Workup

  1. stirringthe mixture is stirred for a further 20 minutes
  2. stirringThe mixture is then stirred for a further 20 minutes at −25° C
  3. filtrationThe suspension is filtered
  4. washwashed once with 10 ml of methylcyclohexane and twice with 10 ml of water in each case
  5. customDrying

Sources & evidence

ORD record
ord-68a189e641bf4cf2a77c3894163c0462
Source dataset
uspto-grants-2013_06
Patent number
US08455657B2

Reaction notes

Loading…