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Boron trifluoride etherate → Ethyl 8-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-1,4-dithiaspiro[4.5]dec-6-ene-7-carboxylate

HRID 546339
Notes
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Reaction equation

HRID 546339 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][C:16](=O)[CH2:15][CH2:14]1)(=[O:12])=[O:11].[CH2:25]([SH:28])[CH2:26][SH:27].B(F)(F)F.CCOCC.[OH-].[Na+]>ClCCl.CCCCCC>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[CH2:14][CH2:15][C:16]2([S:28][CH2:25][CH2:26][S:27]2)[CH:17]=[C:18]1[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:12])=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 14798Sodium HydroxideHCID 57870910Ethyl 6-(N-(2-chloro-4-fluorophenyl)sulfamoyl)-3-oxocyclohex-1-ene-1-carboxylate

Product 1

HCID 57871022Ethyl 8-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-1,4-dithiaspiro[4.5]dec-6-ene-7-carboxylateYield 266.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

100 mg (0.27 mmol) of ethyl 6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]-3-oxo-1-cyclohexene-1-carboxylate obtained in Example 7 was dissolved in 1 ml of dichloromethane and 0.034 ml (0.405 mmol) of ethane-1,2-dithiol and 0.025 ml (0.203 mmol) of boron trifluoride diethyl etherate were added thereto with stirring under ice-cooling, followed by stirring at room temperature for 1 hour. To the reaction solution was added a 1N aqueous sodium hydroxide solution and the mixture was extracted with diethyl ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The resulting solid was washed with diethyl ether and then with hexane to give 325 mg of the title compound as a white powder (76% yield).

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 1 hour
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. washThe resulting solid was washed with diethyl ether

Sources & evidence

ORD record
ord-66243744ab6d431688b63452b28de7ab
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935835B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes