4-Chlorobenzenesulfonyl chloride → HCID 67302979, compound

HRID 2061601Notes

Reaction equation

HRID 2061601 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15]([CH:17]1[CH2:27][CH:26]2[N:28]([S:29]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)(=[O:31])=[O:30])[CH:19]([CH2:20][C:21]3[NH:22][N:23]=[CH:24][C:25]=32)[CH2:18]1)=[O:16])[CH3:13]>N1C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:22]2[C:21]3[CH2:20][CH:19]4[N:28]([S:29]([C:32]5[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=5)(=[O:31])=[O:30])[CH:26]([C:25]=3[CH:24]=[N:23]2)[CH2:27][CH:17]([C:15]([O:14][CH2:12][CH3:13])=[O:16])[CH2:18]4)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:23]2[CH:24]=[C:25]3[CH:26]4[N:28]([S:29]([C:32]5[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=5)(=[O:30])=[O:31])[CH:19]([CH2:20][C:21]3=[N:22]2)[CH2:18][CH:17]([C:15]([O:14][CH2:12][CH3:13])=[O:16])[CH2:27]4)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 16045395HCID 16045395, compound

Product 2

HCID 67302979HCID 67302979, compoundYield 116.3%HCID 67308838HCID 67308838, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

4-Chlorobenzenesulfonyl chloride (0.315 g, 1.49 mmol) was added to a solution of ethyl 10-(4-chlorophenyl)sulfonyl-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazole-6-carboxylate (8) (0.51 g, 1.24 mmol) in pyridine (5 mL) and the resulting mixture was stirred at room temperature for 1 h. The resulting solution was diluted with CH2Cl2 and washed with aqueous 1N Ha then saturated aqueous NaHCO3. The organic phase was dried (Na2SO4), filtered, concentrated and purified by silica gel column chromatography (eluant hexane/EtOAc, 20/1 to 1/1) to give ethyl 1,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazole-6-carboxylate and ethyl 2,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-2H-4,8-epiminocycloocta[c]pyrazole-6-carboxylate (57) (0.721 mmol, 1.23 mmol, quant). MS (ESI) 584.0 (M+H).

Workup

  1. washwashed with aqueous 1N Ha
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (eluant hexane/EtOAc, 20/1 to 1/1)

Sources & evidence

ORD record
ord-4f286b4c68da4613b5a81ccb6024d984
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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