Potassium Carbonate → (2Z)-2-[(2-amino-1,3-thiazol-4-yl)methoxyimino]-N-hydroxy-2-(3-methoxyphenyl)-N-methylethanimidamide

HRID 520251Notes

Reaction equation

HRID 520251 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]C=C(OC)C=2)\[C:11]#[N:12])[N:6]=1.[C:21](=O)([O-])[O-].[K+].[K+].Cl.[CH3:28][NH:29][OH:30].[CH3:31][CH:32]([OH:34])[CH3:33].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:33]=[C:32]([O:34][CH3:21])[CH:31]=2)\[C:11](=[NH:12])[N:29]([OH:30])[CH3:28])[N:6]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 77906N-methylhydroxylamine hydrochlorideHCID 21889133Propan-2-ol--water (1/1)HCID 89655523(1Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]-3-methoxybenzenecarboximidoyl cyanide

Product 1

HCID 89656222(2Z)-2-[(2-amino-1,3-thiazol-4-yl)methoxyimino]-N-hydroxy-2-(3-methoxyphenyl)-N-methylethanimidamideYield 69%

Conditions

Temperature
80 °C

Procedure

To a solution of (2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(3-methoxyphenyl)acetonitrile (4.00 g, 13.87 mmol, 1 eq.) in 2-propanol/water (60 ml/16 ml), was added potassium carbonate (3.84 g, 27.75 mmol, 2.0 eq) and N-methylhydroxylamine hydrochloride (2.32 g, 27.75 mmol, 2 eq.). The reaction was heated under stirring to 80° C. for 2 h. The residue was extracted with EtOAc and washed with water. The organics were combined, dried over MgSO4 and concentrated to give (2Z)-2-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}-N-hydroxy-N-methyl-2-(3-methoxyphenyl)ethanimidamide (3.36, 69% yield), as a yellow solid.

Workup

  1. temperatureThe reaction was heated
  2. extractionThe residue was extracted with EtOAc
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e75c7053610b480ab70838b0eda414b4
Source dataset
uspto-grants-2016_05
Patent number
US09326515B2

Reaction notes

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