Sodium Iodide → HCID 18963346, compound

HRID 1707466Notes

Reaction equation

HRID 1707466 reaction equation
[C:1]([N:20]1[CH:24]=[C:23](CO)[N:22]=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27](N(CC)CC)C.[CH3:34][S:35](Cl)(=O)=O.[S:39]1C=CC=[C:40]1[CH2:44][C:45]([O-:47])=O.[K+].[I-].[Na+]>ClCCl.CN(C)C=O.O.CC(C)=O>[C:45]([CH2:44][C:40]([S:35][CH2:34][C:23]1[N:22]=[N:21][N:20]([C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:24]=1)=[S:39])(=[O:47])[CH3:27]

Participants

10

Reactant 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13471695[1-(Triphenylmethyl)-1H-1,2,3-triazol-4-yl]methanolHCID 23696799Potassium 2-thienylacetate

Product 1

HCID 18963346HCID 18963346, compoundYield 86%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-trityl-1,2,3-triazol-4-ylmethanol (8.00 g: 23.5 mMol.) in a mixture of dichloromethane (150 ml) and dimethylformamide (15 ml) at -40° C. are added triethylamine (3.9 ml: 28.0 mMol.) and methanesulfonyl chloride (2.2 ml: 28.4 mMol.), and the mixture is stirred at -30° to -40° C. for 25 minutes. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, and concentrated. To a solution of the residue in acetone (150 ml) are added potassium thiol-acetate (4.02 g: 35.2 mMol.) and sodium iodide (7.03 g: 46.9 mMol.), and the mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with water and brine, dried over sodium sulfate, and concentrated. The resulting crystals are washed with ether to give 4-acetylthioacetylthiomethyl- 1-trityl-1,2,3-triazole (8.01 g) as white crystals. Yield: 86%. mp. 172° to 173° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. stirringthe mixture is stirred at room temperature for 2 hours
  6. extractionextracted with ethyl acetate
  7. washThe extract is washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. washThe resulting crystals are washed with ether

Sources & evidence

ORD record
ord-10a713a6f0c4499c8049537f41b640e3
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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