2-Naphthylisothiocyanate → 5-Amino-2-(naphthalen-2-ylamino)thiazole-4-carboxamide

HRID 512526Notes

Reaction equation

HRID 512526 reaction equation
[NH2:1][CH:2]([C:6]#[N:7])[C:3]([NH2:5])=[O:4].[N:8]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)=[C:9]=[S:10]>CCOC(C)=O>[NH2:7][C:6]1[S:10][C:9]([NH:8][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)=[N:1][C:2]=1[C:3]([NH2:5])=[O:4]

Participants

4

Reactant 2

HCID 742222-NaphthylisothiocyanateHCID 983412-Amino-2-cyanoacetamide

Product 1

HCID 867033695-Amino-2-(naphthalen-2-ylamino)thiazole-4-carboxamideYield 78.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2-amino-2-cyanoacetamide (0.486 g, 2.70 mmol) in EtOAc (15 mL), was added 2-isothiocyanatonaphthalene (0.5 g, 2.70 mmol), and the mixture was refluxed for 30 min. The solvent was evaporated under reduced pressure, and the resulting crude residue was purified by silica gel column chromatography eluted with 2% MeOH in DCM to give 0.6 g (78% yield) of the titled compound.

Workup

  1. temperaturethe mixture was refluxed for 30 min
  2. customThe solvent was evaporated under reduced pressure
  3. customthe resulting crude residue was purified by silica gel column chromatography
  4. washeluted with 2% MeOH in DCM

Sources & evidence

ORD record
ord-e09bde594e424d9b9ddb00cffa647485
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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