2-Naphthylisothiocyanate → HCID 86703384, compound

HRID 512550

Reaction equation

HRID 512550 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]=[C:12]=[S:13].[NH2:14][CH:15]([C:21]#[N:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CCO>[NH2:22][C:21]1[S:13][C:12]([NH:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[N:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 742222-NaphthylisothiocyanateHCID 288716Ethyl 2-amino-2-cyanoacetate

Product 1

HCID 86703384HCID 86703384, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-naphthalenyl isothiocyanate (0.5 g, 2.7 mmol) and ethyl 2-amino-2-cyanoacetate (0.38 g, 2.97 mmol) in EtOH (16 mL) was heated at 80° C. for 3 h. The reaction mixture was cooled to rt, and the solvent was concentrated in vacuo. The resulting solids were collected and washed with n-Hexane-EtOAc (1:1) to give 565 mg (67% yield) of the titled compound.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationthe solvent was concentrated in vacuo
  3. customThe resulting solids were collected
  4. washwashed with n-Hexane-EtOAc (1:1)

Sources & evidence

ORD record
ord-725331d5ea464ea1aa8340dfcfb271b1
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Linked notes

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