Hydrochloric Acid → HCID 59713392, compound

HRID 2223044Notes

Reaction equation

HRID 2223044 reaction equation
[NH2:1][C:2]1([CH:8]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([Cl:17])[CH:11]=2)[OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.N1C=CC=CC=1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.Cl>C(Cl)Cl>[Cl:17][C:12]1[CH:11]=[C:10]([CH:8]([OH:9])[C:2]2([NH:1][S:30]([C:27]3[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=3)(=[O:32])=[O:31])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH:15]=[C:14]([Cl:16])[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 59713386HCID 59713386, compound

Product 1

HCID 59713392HCID 59713392, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

To a stirred solution of (1-amino-cyclohexyl)-(3,5-dichloro-phenyl)-methanol and pyridine (100 μL, 1.24 mmol) in CH2Cl2 (4 mL) was added p-toluenesulfonyl chloride. The mixture was heated at ca. 35° C. for 8 hours. The mixture was applied to a 10 mL Chem Elut cartridge pre-wetted with 5% aqueous HCl (5 mL) and eluted with CH2Cl2 (25 mL). The eluate was applied to a second Chem Elut cartridge pre-wetted with saturated aqueous NaHCO3. The eluate from the second cartridge was evaporated to leave N-{1-[(3,5-dichloro-phenyl)-hydroxy-methyl]-cyclohexyl}-4-methyl-benzenesulfonamide (139 mg) as an oil. 1H NMR (500 MHz, CDCl3) δ(ppm): 7.7 (d, 2H), 7.2 (s, 2H), 7.15 (d, 2H), 7.1 (s, 1H), 4.82 (s, 1H), 4.16 (s, 1H), 2.33 (s, 3H), 0.9-1.9 (m, 10H).

Workup

  1. washeluted with CH2Cl2 (25 mL)
  2. customThe eluate from the second cartridge was evaporated

Sources & evidence

ORD record
ord-17a12d954ef74d3982f1b4f524dd5916
Source dataset
uspto-grants-2008_05
Patent number
US07375093B2

Reaction notes

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