Sodium Carbonate → HCID 58542538, compound

HRID 1843102Notes

Reaction equation

HRID 1843102 reaction equation
C(N(S(F)(F)[F:7])CC)C.O[C:11]([C:14]1[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:16]([CH3:28])[N:15]=1)([CH3:13])[CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[F:7][C:11]([C:14]1[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:16]([CH3:28])[N:15]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 58542588HCID 58542588, compound

Product 1

HCID 58542538HCID 58542538, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At −10° C., 0.52 ml (3.9 mmol) of diethylaminosulphur trifluoride is added dropwise to a solution of 1.00 g (3.57 mmol) of ethyl 3-(2-hydroxypropan-2-yl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate in 20 ml of dichloromethane. The mixture is afterstirred for one hour at −10° C., sodium carbonate is added, and the mixture is stirred for 10 minutes at room temperature. After adding saturated sodium carbonate solution, extraction is carried out with dichloromethane, and the combined organic phases are dried over sodium sulphate and concentrated by evaporation in vacuo on a rotary evaporator. Purification by flash chromatography on silica gel (cyclohexane/ethyl acetate) gives 700 mg of ethyl 3-(2-fluoropropan-2-yl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate (67%).

Workup

  1. additionAfter adding saturated
  2. extractionsodium carbonate solution, extraction
  3. dry with materialthe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated by evaporation in vacuo on a rotary evaporator
  5. customPurification by flash chromatography on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-a2382d03240f42948064c0e487af4433
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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