Benzoyl isothiocyanate → HCID 59128801, compound

HRID 2390507Notes

Reaction equation

HRID 2390507 reaction equation
[C:1]([C:5]1[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=1[O:7][C:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:19]([N:27]=[C:28]=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[C:19]([NH:27][C:28]([NH:14][C:13]1[C:8]([O:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[C:1]([CH3:4])([CH3:2])[CH3:3])=[N:9][CH:10]=[CH:11][CH:12]=1)=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 286054272-(2-Tert-butylphenoxy)pyridin-3-amine

Product 1

HCID 59128801HCID 59128801, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(2-tert-Butylphenoxy)-3-aminopyridine (200 mg, 0.82 mmol) and benzoyl isothiocyanate (133 μL, 0.99 mmol, 1.2 eq) in DCM (10 mL) was heated at reflux for 1 h. The mixture was cooled to rt and evaporated to give the crude product. Purification by flash chromatography (silica, 0-50% EtOAc/hexane gradient) provided Example 217a as a white fluffy powder. (M+H)+=406.29.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. customevaporated

Sources & evidence

ORD record
ord-2822bc14c5f74bb98191751571940824
Source dataset
uspto-grants-2012_09
Patent number
US08273772B2

Reaction notes

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