Ethanol → 3-(Benzyloxy)-N-(4-Methyl-1,3-Thiazol-2-Yl)pyridin-2-Amine

HRID 1426086Notes

Reaction equation

HRID 1426086 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:15][C:16]([NH2:18])=[S:17])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:27][C:28](=O)[CH3:29].CCO>O>[CH2:1]([O:8][C:9]1[C:10]([NH:15][C:16]2[S:17][CH:27]=[C:28]([CH3:29])[N:18]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6571ChloroacetoneHCID 8471TriethylamineHCID 727056391-(3-(Benzyloxy)pyridin-2-yl)thiourea

Product 1

HCID 166600153-(Benzyloxy)-N-(4-Methyl-1,3-Thiazol-2-Yl)pyridin-2-AmineYield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1 L round-bottomed flask was charged with 1-(3-(benzyloxy)pyridin-2-yl)thiourea (31.7 g, 122 mmol), triethylamine (29.0 mL, 207 mmol), 1-chloropropan-2-one (13.6 mL, 171 mmol), and EtOH (400 mL). The reaction mixture was heated to reflux overnight, then poured into water and extracted with methylene chloride. The organic layer was dried over sodium sulfate, filtered and concentrated to afford 3-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (32.7 g, 89.9% yield) as a yellow solid. 1H NMR (CDCl3) δ 8.58 (s, 1H), 7.93 (m, 1H), 7.39 (m, 5H), 7.08 (d, 1H), 6.80 (dd, 1H), 6.37 (s, 1H), 5.08 (s, 2H), 2.32 (s, 3H). LCMS (25 to 95) Rt=2.94 min (apci) m/z=298 (M+H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1468b1dea21f4fc794763d42c9a33877
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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