4-Toluenesulfonyl chloride → HCID 89996125, compound

HRID 1480815Notes

Reaction equation

HRID 1480815 reaction equation
[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH2:8][OH:9])[CH:6]=1.C(N(CC)CC)C.[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:24][C:23]1[CH:25]=[CH:26][C:20]([S:17]([O:9][CH2:8][CH2:7][N:5]2[CH:6]=[C:2]([I:1])[CH:3]=[N:4]2)(=[O:19])=[O:18])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 57886737HCID 57886737, compound

Product 1

HCID 89996125HCID 89996125, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-Iodo-1H-pyrazol-1-yl)ethanol (Preparation 57, 535 mg, 2.248 mmol) in DCM (11 mL) was treated with triethylamine (1.55 mL, 11.14 mmol) at 0° C. Tosyl chloride (857 mg, 4.50 mmol) was added at 0° C. and the mixture was allowed to warm to room temperature for 18 hours. The organic layer was washed with water, HCl 1M and water (twice). The organic layers were dried, concentrated and purified by silica gel column chromatography eluting with 0 to 30% EtOAc in cyclohexane to give the title compound (817 mg, 93%).

Workup

  1. washThe organic layer was washed with water, HCl 1M and water (twice)
  2. customThe organic layers were dried
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography
  5. washeluting with 0 to 30% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-b985b8e7aacc4b73828f8e2fee40dcce
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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