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

HRID 6873

Reaction equation

HRID 6873 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-e587e61d27f4401dbb3291711c0d358c
Source dataset
uspto-grants-2006_08
Patent number
US07084160B2

Linked notes

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