Benzenesulfonyl chloride → HCID 58094712, compound

HRID 885458Notes

Reaction equation

HRID 885458 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]([CH3:14])[C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[N:10]=2)=[CH:4][CH:3]=1.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:9]2[N:13]([CH3:14])[C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[N:10]=2)[S:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:27])=[O:26])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 923834HCID 923834, compound

Product 1

HCID 58094712HCID 58094712, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To (4-chloro-phenyl)-(1-methyl-1H-benzimidazol-2-yl)-amine (258 mg, 1.0 mmol) in anhydrous pyridine (4 mL) at room temperature was added benzenesulfonyl chloride (706.5 mg, 4.0 mmol). The resulting mixture was heated to 100° C. in a microwave reactor for 1 h. The resulting mixture was then diluted with EtOAc, washed with 1 N HCl and the organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The resultant residue was purified by flash column chromatography (SiO2), eluting with a hexanes-EtOAc gradient to yield the title compound as a crude residue, which was dissolved in ether containing 2.0M hydrogen chloride, and then concentrated in vacuo to yield the title compound as its corresponding HCl salt. MS 398 (M+1)+

Workup

  1. washwashed with 1 N HCl
  2. dry with materialthe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by flash column chromatography (SiO2)
  6. washeluting with a hexanes-EtOAc gradient

Sources & evidence

ORD record
ord-dd12bb190df44031a7d2dea0cdaff579
Source dataset
uspto-grants-2012_08
Patent number
US08242157B2

Reaction notes

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