Dimethylformamide → HCID 178477163, compound

HRID 249578Notes

Reaction equation

HRID 249578 reaction equation
[NH:1]1[C:5]([SH:6])=[N:4][N:3]=[N:2]1.[H-].[Na+].[S:9]1[CH:13]=C[CH:11]=[C:10]1CC(OCCl)=O.CN(C)C=[O:23]>Cl.O>[C:10]([S:9][CH2:13][S:6][C:5]1[NH:4][N:3]=[N:2][N:1]=1)(=[O:23])[CH3:11]

Participants

7

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 57186933Chloromethyl thiolacetateHCID 178527994HCID 178527994, compound

Product 1

HCID 178477163HCID 178477163, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a solution of tetrazole-5-thiol (3.00 g : 29.41 mMol.) in dimethylformamide (50 ml) under ice cooling is added sodium hydride (60% suspension in oil : 2.59 q : 64.75 mMol.), and the mixture is stirred under ice cooling for 5 to 6 minutes. To the mixture is added a solution of chloromethyl thiolacetate (4.39 gi 35.26 mMol.) in dimethylformamide (10 ml), and the mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with 10% hydrochloric acid (11 ml) and water and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue is purified by silica gel column chromatography (toluene : ethyl acetate=1:1) and the resulting residue is washed with a mixture of n-hexane and ether to give 5-acetylthiomethylthiotetrazole (2.49 9) as colorless crystals. Yield : 45%, m.p. 90° C.

Workup

  1. stirringthe mixture is stirred at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography (toluene : ethyl acetate=1:1)
  8. washthe resulting residue is washed with a mixture of n-hexane and ether

Sources & evidence

ORD record
ord-7c1bf5f5d3c2465f9a5cb5db75c2847b
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Reaction notes

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