Diisopropylethylamine → HCID 76223275, compound

HRID 1853968Notes

Reaction equation

HRID 1853968 reaction equation
[S:1]1[C:5]([C:6]#[N:7])=[CH:4][N:3]=[CH:2]1.Cl.[NH2:9][OH:10].CCN(C(C)C)C(C)C>CCO>[S:1]1[C:5]([C:6](=[N:9][OH:10])[NH2:7])=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 216249491,3-Thiazole-5-carbonitrile

Product 1

HCID 76223275HCID 76223275, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (3.07 g, 44 mmol) was added to a solution of 1,3-thiazole-5-carbaldehyde (5 g, 44 mmol) and pyridine (3.7 mL) in DCM (25 mL). The reaction mixture was stirred overnight at room temperature and then washed once with water. The product was recovered by filtration to give 5.23 g of 1,3-thiazole-5-carbaldehyde oxime (yield 92%). 1,3-thiazole-5-carbaldehyde oxime (2.5 g, 19.5 mmol, 1 equiv) was dissolved in 12 mL of dioxane and then TEA (6.8 mL, 2.5 equiv) was added. The reaction mixture was cooled to 0° C. and then trifluoroacetic anhydride (3.0 mL, 1.1 equiv) was added dropwise to the reaction. The solution was stirred overnight at room temperature and then 1.1 equivalent of trifluoroacetic anhydride was added to complete the reaction. The solution was stirred overnight at room temperature and then evaporated. The residue was dissolved in DCM and then washed five times with water. The organic layer was dried over MgSO4 and then evaporated under reduced pressure to give 1.25 g of 1,3-thiazole-5-carbonitrile (Yield 58%). 1,3-thiazole-5-carbonitrile (1 g, 9.08 mmol, 1 equiv), hydroxylamine hydrochloride (0.95 g, 1.5 equiv) and DIEA (2.5 mL, 1.6 equiv) were mixed in absolute EtOH (30 mL). The reaction mixture was refluxed 5 h and then the solvent was evaporated under reduced pressure. The residue was dissolved in AcOEt, washed twice with water and once with brine. The organic layer was dried over MgSO4 and then evaporated under reduced pressure to give 940 mg of 1,3-thiazole-5-amidoxime (yield 72%).

Workup

  1. temperatureThe reaction mixture was refluxed 5 h
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in AcOEt
  4. washwashed twice with water and once with brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d89ca4c1db0b45b19287aeb3e0d924c9
Source dataset
uspto-grants-2015_02
Patent number
US08962658B2

Reaction notes

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