Hydrochloric Acid → 4-Oxobicyclo[3.2.1]oct-2-en-2-yl 2-methyl-3-methylsulfinyl-4-trifluoromethylbenzoat

HRID 1045119Notes

Reaction equation

HRID 1045119 reaction equation
[CH3:1][C:2]1[C:10]([S:11]([CH3:13])=[O:12])=[C:9]([C:14]([F:17])([F:16])[F:15])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:18]12[CH2:25][CH:22]([CH2:23][CH2:24]1)[C:21](=[O:26])[CH2:20][C:19]2=O.Cl.CN(C)CCCN=C=NCC.Cl>ClCCl>[CH3:1][C:2]1[C:10]([S:11]([CH3:13])=[O:12])=[C:9]([C:14]([F:15])([F:17])[F:16])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:19]1[CH:18]2[CH2:25][CH:22]([C:21](=[O:26])[CH:20]=1)[CH2:23][CH2:24]2)=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 144686Bicyclo(3.2.1)octane-2,4-dioneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66679876HCID 66679876, compound

Product 1

HCID 666793074-Oxobicyclo[3.2.1]oct-2-en-2-yl 2-methyl-3-methylsulfinyl-4-trifluoromethylbenzoat

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

250 mg (0.94 mmol) of 2-methyl-3-(methylsulfinyl)-4-(trifluoromethyl)benzoic acid were introduced into 25 ml of dry dichloromethane. Thereafter 143 mg (1.03 mmol) of bicyclo[3.2.1]octane-2,4-dione and subsequently, in portions, 216 mg (1.13 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added. The mixture was stirred at room temperature for 16 hours and then admixed with 5 ml of 1M hydrochloric acid. Following phase separation, the organic phase was freed from the solvent on a rotary evaporator. The residue was purified by chromatography, with 170 mg of clean product being isolated.

Workup

  1. customFollowing phase separation
  2. customthe organic phase was freed from the solvent on a rotary evaporator
  3. customThe residue was purified by chromatography, with 170 mg of clean product
  4. custombeing isolated

Sources & evidence

ORD record
ord-ae50c2b88f9c46cab70688e9fd089b86
Source dataset
uspto-grants-2013_10
Patent number
US08563779B2

Reaction notes

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