Pyridine → 2-phenylethyl N-[4-[[(Z)-[cyano(phenyl)methylidene]amino]oxymethyl]-1,3-thiazol-2-yl]carbamate

HRID 520256Notes

Reaction equation

HRID 520256 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.N1C=CC=CC=1.[C:25]1([CH2:31][CH2:32][O:33][C:34](Cl)=[O:35])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[C:11](/[C:10](=[N:9]\[O:8][CH2:7][C:5]1[N:6]=[C:2]([NH:1][C:34](=[O:35])[O:33][CH2:32][CH2:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[S:3][CH:4]=1)/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)#[N:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 159175902-Phenylethyl chloroformateHCID 89443882(Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]benzenecarboximidoyl cyanide

Product 1

HCID 896557582-phenylethyl N-[4-[[(Z)-[cyano(phenyl)methylidene]amino]oxymethyl]-1,3-thiazol-2-yl]carbamateYield 76.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile (1 g, 3.87 mmol, 1 eq.) in dry dichloromethane (15 ml) at room temperature was added pyridine (0.38 ml, 4.65 mmol, 1.2 eq). After stirring for 15 min at room temperature 2-phenylethylcarbonochloridate (858 mg, 4.65 mmol, 1.2 eq) was added and stirring was allowed during 5 h. The reaction was quenched by addition of water and concentrated to dryness. The residue was taken in DCM (5 mL) and 5 ml of 1N NaOH was added. The layers were separated and the organic phase was dried over MgSO4 then concentrated to give 2-phenylethyl {4-[({[(Z)-cyano(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-yl}carbamate (1.2 g, 55% yield) which was used in the next step without further purification.

Workup

  1. additionwas added
  2. customThe reaction was quenched by addition of water
  3. concentrationconcentrated to dryness
  4. addition5 ml of 1N NaOH was added
  5. customThe layers were separated
  6. dry with materialthe organic phase was dried over MgSO4
  7. concentrationthen concentrated

Sources & evidence

ORD record
ord-98a606b9daef4228a3874a763e365694
Source dataset
uspto-grants-2016_05
Patent number
US09326515B2

Reaction notes

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