Water → HCID 68430346, compound

HRID 2267164Notes

Reaction equation

HRID 2267164 reaction equation
[C:1]1([N:7]2[CH:11]=[C:10]([Si](C)(C)C)[NH:9][N:8]2C(N)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1C=CC(S(Cl)(=O)=O)=CC=1.O.[N:31]1C=CC=C[CH:32]=1>>[C:1]1([N:7]2[C:11]([C:32]#[N:31])=[CH:10][NH:9][NH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 68428264HCID 68428264, compound

Product 1

HCID 68430346HCID 68430346, compound

Conditions

Temperature
130 °C

Procedure

3-phenyl-5-trimethylsilanyl-1H-[1,2,3]triazole-2-carboxylic acid amide (550 mg) which is the compound prepared in the above 3) was dissolved in 2.0 ml of pyridine, 801 mg of 4-methylbenzenesulfonic acid chloride was added thereto and the mixture was stirred at 130° C. for one day. Water was added to the reaction solution, the mixture was extracted with ethyl acetate and the ethyl acetate layer washed with a saturated saline solution and dried over sodium sulfate. After the solvent was evaporated in vacuo and the residue was separated and purified by a thin-layer chromatography (hexane/ethyl acetate=5/1) to give 113 mg of the title compound as a white solid.

Workup

  1. customprepared in the above 3)
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe ethyl acetate layer washed with a saturated saline solution
  4. dry with materialdried over sodium sulfate
  5. customAfter the solvent was evaporated in vacuo
  6. customthe residue was separated
  7. custompurified by a thin-layer chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-3701f5438a7f4352a6006ecee5d27d40
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

Loading…