Potassium Carbonate → (2Z)-2-[(2-amino-1,3-thiazol-4-yl)methoxyimino]-N'-hydroxy-2-phenylethanimidamide
Reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)\[C:11]#[N:12])[N:6]=1.Cl.[NH2:20][OH:21].C(=O)([O-])[O-].[K+].[K+]>CC(O)C.O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)\[C:11](=[N:20]\[OH:21])\[NH2:12])[N:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a suspension of (2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile (4.5 g, 17.42 mmol, 1 eq.) in iPrOH/H2O (10/1, 110 ml) were added hydroxylamine hydrochloride (3.63 g, 52.26 mmol, 3 eq.) and potassium carbonate (7.22 g, 52.2 mmol, 3 eq.). The reaction was heated to 80° C. for 6 h and the solvent was evaporated to ¾th. The residue was extracted with EtOAc (3×50 ml) and washed with aq. sat. NaCl. The organics were combined, dried over MgSO4 and concentrated to give (1Z,2Z)-2-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}-N′-hydroxy-2-phenylethanimidamide (5.86 g) as a white solid.
Workup
- customthe solvent was evaporated to ¾th
- extractionThe residue was extracted with EtOAc (3×50 ml)
- washwashed with aq. sat. NaCl
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c69e3b2b68314075b07885a671a09263
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090600B2
Reaction notes
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