Water → 4-(Azidomethyl)-2-thiazolamine

HRID 2276160Notes

Reaction equation

HRID 2276160 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([NH2:8])[S:6][CH:7]=1.O.[N-:10]=[N+:11]=[N-:12].[Na+]>O1CCOCC1>[N:10]([CH2:2][C:3]1[N:4]=[C:5]([NH2:8])[S:6][CH:7]=1)=[N+:11]=[N-:12]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 732294-Chloromethylthiazol-2-ylamine

Product 1

HCID 534165784-(Azidomethyl)-2-thiazolamineYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-chloromethyl-thiazol-2-ylamine (7.45 g, 50.0 mmol) in dioxane:water mixture (8:2) was added sodium azide (4.87 g, 75.0 mmol) and the reaction mixture was refluxed for 2-3 h. The mixture was concentrated in vacuo to remove all dioxane and the residue was dissolved in EtOAc (200 mL). The organic layer was washed with water (2×200 mL), brine (2×200 mL), dried over (Na2SO4) and concentrated in vacuo to give 4-azidomethyl-thiazol-2-ylamine in 70-90% yield.

Workup

  1. temperaturethe reaction mixture was refluxed for 2-3 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customto remove all dioxane
  4. dissolutionthe residue was dissolved in EtOAc (200 mL)
  5. washThe organic layer was washed with water (2×200 mL), brine (2×200 mL)
  6. dry with materialdried over (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1cb7a25634584fcd8aac585bc746eee4
Source dataset
uspto-grants-2015_09
Patent number
USRE045670E1

Reaction notes

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