2-Amino-4-methylpyridine → N-[(4-methylpyridin-2-yl)carbamothioyl]benzamide

HRID 1985757

Reaction equation

HRID 1985757 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[C:9]([N:17]=[C:18]=[S:19])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CC(C)=O>[C:9]([NH:17][C:18]([NH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1)=[S:19])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 68284Benzoyl isothiocyanate

Product 1

HCID 881443N-[(4-methylpyridin-2-yl)carbamothioyl]benzamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-amino-4-methylpyridine (1.08 g, 10 mmol) and benzoyl isothiocyanate (1.63 g, 10 mmol) in acetone (15 mL) was stirred at RT for 1.5 h. The precipitate formed was filtered and washed with acetone to afford 1-benzoyl-3-[4-methylpyridin-2-yl]-thiourea as a solid. This material was stirred with 2 N NaOH solution (15 mL) at 110° C. for 1 h, then cooled to RT, and the precipitate formed was washed with water and dried to provide (4-methylpyridin-2-yl)-thiourea (0.90 g, 53%). MS m/z 168 (M+H)+.

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered
  3. washwashed with acetone

Sources & evidence

ORD record
ord-302fe9a461e84494bf6c4cc40a9d79b4
Source dataset
uspto-grants-2009_06
Patent number
US07547711B2

Linked notes

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