Bromochloromethane → HCID 10049185, compound

HRID 249614Notes

Reaction equation

HRID 249614 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([CH2:25][SH:26])[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.[H-].[Na+].Br[CH2:30]Cl.[C:32]([O-:35])(=[S:34])[CH3:33].[K+]>CN(C)C=O.O.CC(C)=O>[C:32]([S:34][CH2:30][S:26][CH2:25][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:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:24]=1)(=[O:35])[CH3:33]

Participants

8

Reactant 4

HCID 6333BromochloromethaneHCID 24758Sodium hydrideHCID 9975616HCID 9975616, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 10049185HCID 10049185, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1-trityl-1,2,3-triazol-4-ylmethylmercaptan (3.00 g : 8.40 mMol.) in dimethylformamide (10 ml) is added sodium hydride (60% dispersion in oil : 370 mg : 9.25 mMol.), and the mixture is stirred for 5 minutes at room temperature. The reaction mixture is added to a solution of bromochloromethane (15 ml) in dimethylformamide (15 ml) at -30° C., and the mixture is stirred at -20° C. to -30° C. for 30 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 (30 ml) is added potassium thioacetate (1.92 g : 16.8 mMol.), and the mixture is stirred at room temperature for 1 hour. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with water, dried over sodium sulfate, and concentrated. The residue is purified by silica gel chromatography (toluene : ethyl acetate=10:1) and crystallized from ether to give 4-acetylthiomethylthiomethyl-1-trityl-1,2,3-triazole (2.65 g) as colorless crystals. Yield: 71%. mp. 106° C.

Workup

  1. stirringthe mixture is stirred at -20° C. to -30° C. for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. stirringthe mixture is stirred at room temperature for 1 hour
  7. extractionextracted with ethyl acetate
  8. washThe extract is washed with water
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customThe residue is purified by silica gel chromatography (toluene : ethyl acetate=10:1)
  12. customcrystallized from ether

Sources & evidence

ORD record
ord-f0486899548946f0b616d67a85ab249a
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Reaction notes

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