Sodium Hydroxide → 1-(3-(Benzyloxy)-5-bromopyridin-2-yl)thiourea

HRID 1426082Notes

Reaction equation

HRID 1426082 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[C:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][C:16]([Br:27])=[CH:15][N:14]=1)=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+]>O>[CH2:20]([O:19][C:18]1[C:13]([NH:12][C:10]([NH2:9])=[S:11])=[N:14][CH:15]=[C:16]([Br:27])[CH:17]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 866396501-Benzoyl-3-(3-(benzyloxy)-5-bromopyridin-2-yl)thiourea

Product 1

HCID 727056401-(3-(Benzyloxy)-5-bromopyridin-2-yl)thioureaYield 92.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1 L round-bottom flask was charged with 1-benzoyl-3-(3-(benzyloxy)-5-bromopyridin-2-yl)thiourea (17.9 g, 40.5 mmol) and 3M sodium hydroxide (3.3 mL, 9.9 mmol), and the reaction mixture was refluxed overnight. The reaction mixture was then cooled, poured into water, and filtered to provide 1-(3-(benzyloxy)-5-bromopyridin-2-yl)thiourea (12.6 g, 92.2% yield) as a yellow solid. 1H NMR (CDCl3) δ 10.60 (bs, 1H), 8.59 (bs, 1H), 7.87 (d, 1H), 7.40 (m, 5H), 7.30 (d, 1H), 6.90 (m, 1H), 5.15 (s, 2H). Mass spectrum (apci) m/z=340.0 (M+H).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. temperatureThe reaction mixture was then cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-8fc37007cb4b49b8be39c803ddc45e07
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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