Ethanol → 1-(3-(Benzyloxy)pyridin-2-yl)thiourea

HRID 1426085Notes

Reaction equation

HRID 1426085 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][CH:16]=[CH:15][N:14]=1)=[S:11])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].CCO>O>[CH2:20]([O:19][C:18]1[C:13]([NH:12][C:10]([NH2:9])=[S:11])=[N:14][CH:15]=[CH:16][CH:17]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 727056381-Benzoyl-3-(3-(benzyloxy)pyridin-2-yl)thiourea

Product 1

HCID 727056391-(3-(Benzyloxy)pyridin-2-yl)thioureaYield 109.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1 L round-bottomed flask was charged with 1-benzoyl-3-(3-(benzyloxy)pyridin-2-yl)thiourea (44.4 g, 122 mmol), potassium carbonate (20.3 g, 147 mmol), and EtOH (400 mL). The reaction mixture was heated to reflux overnight, then cooled, poured into water (900 mL) and filtered to afford 1-(3-(benzyloxy)pyridin-2-yl)thiourea (34.6 g) as a yellow solid. 1H NMR (CDCl3) δ 11.01 (s, 1H), 8.69 (s, 1H), 7.78 (d, 1H), 7.44-7.34 (m, 5H), 7.16 (d, 1H), 7.09 (bs, 1H), 6.91 (dd, 1H), 5.16 (s, 2H). LCMS (25 to 95) Rt=2.06 min (apci) m/z=260 (M+H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. temperaturecooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-3aa6bdf0af464e5f824d6ff088335fe2
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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