Sodium Hydroxide → N-(4-methoxyphenyl)-4-pyridin-4-yl-1,3-thiazol-2-amine

HRID 1592967

Reaction equation

HRID 1592967 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)=O.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH2:22])=[S:21])=[CH:15][CH:14]=1.[OH-].[Na+]>O.CCO>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20]2[S:21][CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=3)[N:22]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4070312-Bromo-1-(pyridin-4-yl)ethanoneHCID 6675494-Thioureidoanisole

Product 1

HCID 793675N-(4-methoxyphenyl)-4-pyridin-4-yl-1,3-thiazol-2-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 3.0 g (15 mmol) 4-(2-bromo)acetylpyridine (6-2) in 50 mL water was added an equimolar amount of 4-methoxyphenylthiourea (7-1; 2.75 g). The reaction was diluted with 20 mL EtOH. The reaction was allowed to stir at rt overnight, over which time a color change occurred from clear to a thick orange precipitate. The reaction mixture was diluted with 100 mL water then the pH was adjusted to neutral with 1N NaOH. The reaction was allowed to stir at rt and a large amount of precipitate formed which was collected by filtration. The resulting powder was dried under high vacuum to yield N-(4-methoxyphenyl)-4-pyridin-4-yl-1,3-thiazol-2-amine (7-2): 1H NMR (500 MHz, CD3OD) δ 8.98 (d, J=3 Hz, 2H), 8.10 (d, J=3 Hz, 2H), 7.53 (s, 1H), 3.0 (s, 3H): MS 284.3 found 284.2 (M+H+).

Workup

  1. stirringto stir at rt
  2. customa large amount of precipitate formed which
  3. filtrationwas collected by filtration
  4. customThe resulting powder was dried under high vacuum

Sources & evidence

ORD record
ord-a5e9366d433941d3b9570efba81fe766
Source dataset
uspto-grants-2007_11
Patent number
US07294640B2

Linked notes

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