Acetic Acid → N-Butyl-2-thiazolamine
Reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH:7](=O)[CH2:8][CH2:9][CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C>[CH2:7]([NH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1)[CH2:8][CH2:9][CH3:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
2-aminothiazole (1 g, 10 mmol) and butyraldehyde (1.44 g, 20 mmol) were mixed in dichloroethane (45 ml) and then treated with sodium triacetoxyborohydride (6 g, 28 mmol) and acetic acid (3.6 g 60 mmol). The reaction mixture was stirred at r.t. under a nitrogen atmosphere overnight. The reaction mixture then was quenched by 1N NaOH and extracted with EtOAc. The organic layer was washed with saturated NaHCO3, brine and dried over MgSO4. The solvent was evaporated to give 2-butylaminothiazole as a brown residue (1.02 g).
Workup
- customThe reaction mixture then was quenched by 1N NaOH
- extractionextracted with EtOAc
- washThe organic layer was washed with saturated NaHCO3, brine
- dry with materialdried over MgSO4
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-0826a46927fe409a9774eb8571f4d34d
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07524969B2
Reaction notes
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