Hydrochloric Acid → HCID 58381272, compound

HRID 39417Notes

Reaction equation

HRID 39417 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([S:26][CH3:27])[C:4]=1[C:5]([NH:7][CH:8]1[CH2:17][O:16][CH2:15][CH2:14][C:9]21OCC[O:10]2)=[O:6].Cl>O1CCCC1.O1CCOCC1.O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[CH3:1][O:2][C:3]1[CH:21]=[C:20]([C:22]([F:25])([F:23])[F:24])[CH:19]=[C:18]([S:26][CH3:27])[C:4]=1[C:5]([NH:7][CH:8]1[C:9](=[O:10])[CH2:14][CH2:15][O:16][CH2:17]1)=[O:6]

Participants

8

Reactant 2

HCID 313Hydrochloric AcidHCID 583813042-methoxy-6-methylsulfanyl-4-trifluoromethyl-N-(1,4,8-trioxa-spiro[4.5]dec-6-yl)-benzamide2×

Product 1

HCID 58381272HCID 58381272, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-Methoxy-6-methylsulfanyl-4-trifluoromethyl-N-(1,4,8-trioxa-spiro[4.5]dec-6-yl)-benzamide (intermediate B, 200 mg, 0.49 mmol) was dissolved in 1 mL tetrahydrofuran and 1 mL 4N HCl in dioxane was added. The reaction mixture was refluxed for 2 h. The mixture was diluted with water, ethyl acetate and neutralized with saturated sodium bicarbonate solution. The mixture was extracted two times with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered and evaporated. The crude product was used for the next step.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. extractionThe mixture was extracted two times with ethyl acetate
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-9fcbd94f41c7478792f59f836308b819
Source dataset
uspto-grants-2013_09
Patent number
US08524909B2

Reaction notes

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