1-(Chlorosulfanyl)-2,3,4,5,6-pentafluorobenzene → HCID 12832379, compound

HRID 1995231Notes

Reaction equation

HRID 1995231 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[CH:16][N:17]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)[C:18]=2[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:10][CH:9]=1.[F:33][C:34]1[C:39]([S:40]Cl)=[C:38]([F:42])[C:37]([F:43])=[C:36]([F:44])[C:35]=1[F:45]>CCCCCC.C1(C)C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:15]=[C:16]([S:40][C:39]3[C:38]([F:42])=[C:37]([F:43])[C:36]([F:44])=[C:35]([F:45])[C:34]=3[F:33])[N:17]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)[C:18]=2[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:12][CH:13]=1

Participants

8

Reactant 3

HCID 1197491-(Chlorosulfanyl)-2,3,4,5,6-pentafluorobenzeneHCID 12832387HCID 12832387, compoundHCID 178418339Butyllithium

Product 1

HCID 12832379HCID 12832379, compound

Reagents, catalysts & solvents 4

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under agitation and using argon as the protective gas, 15 ml of about 1.6 N n-butyllithium in hexane, diluted with 30 ml of toluene, is added dropwise at -5° to 0° to a solution of 8.83 g of 4,5-bis(4-methoxyphenyl)-1-(tetrahydropyran-2-yl)imidazole in a mixture of 75 ml of absolute tetrahydrofuran and 75 ml of toluene. After 20 minutes, the pentafluorophenylsulfenyl chloride solution is added dropwise to the reaction mixture, maintaining the temperature between -5° and 0° by cooling. After 2 hours' stirring at room temperature, the solution is diluted with 200 ml of ethyl acetate, washed with sodium bicarbonate solution; the organic solution is dried over sodium sulfate and concentrated to dryness under vacuum. The residue is purified by chromatography on aluminum oxide, neutral, activity stage II, with hexane/ethyl acetate. Recrystallization from ethyl acetate/hexane yields 8.86 g of 4,5-bis(4-methoxyphenyl)-1-(tetrahydropyran-2-yl)-2-(pentafluorophenylthio)imidazole, mp 156°-158°.

Workup

  1. temperaturemaintaining the temperature between -5° and 0°
  2. temperatureby cooling
  3. washwashed with sodium bicarbonate solution
  4. dry with materialthe organic solution is dried over sodium sulfate
  5. concentrationconcentrated to dryness under vacuum
  6. customThe residue is purified by chromatography on aluminum oxide
  7. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b3dea93918cb4f3e8996773998fd67ec
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

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