Pyridine → 5-Bromo-2-chloro-N-(4-hydroxy-cyclohexyl)-benzenesulfonamide

HRID 2382600Notes

Reaction equation

HRID 2382600 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:12])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.N1C=CC=CC=1.[NH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][CH2:21]1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:12])=[C:6]([S:8]([NH:19][CH:20]2[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]2)(=[O:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 509888345-Bromo-2-chlorobenzene-1-sulfonyl chloride2×HCID 178511715HCID 178511715, compound

Product 1

HCID 686319385-Bromo-2-chloro-N-(4-hydroxy-cyclohexyl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Bromo-2-chloro-benzenesulfonyl chloride (1.0 g, 3.45 mmol) (Intermediate E, Step 1) and pyridine (2 ml) are added to a stirred suspension of trans-4-aminocyclohexanol (2.0 g, 17.2 mmol) suspended in DCM (20 ml). After 18 h, the solvents are removed and the residue is partitioned between aq. 1M HCl and ethyl acetate. The organic extract is dried over Mg2SO4 and the solvent is removed. The residue is purified by chromatography on silica, eluting with ethyl acetate:hexane (1:1 to 1:0) to give the title compound.

Workup

  1. customthe solvents are removed
  2. customthe residue is partitioned between aq. 1M HCl and ethyl acetate
  3. extractionThe organic extract
  4. dry with materialis dried over Mg2SO4
  5. customthe solvent is removed
  6. customThe residue is purified by chromatography on silica
  7. washeluting with ethyl acetate:hexane (1:1 to 1:0)

Sources & evidence

ORD record
ord-db2f5d21d1d34046a936b81625870e6c
Source dataset
uspto-grants-2012_09
Patent number
US08263585B2

Reaction notes

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