Ethanol → 5-bromo-N-(4-methylthiazol-2-yl)-3-(phenylthio)pyridin-2-amine

HRID 335127Notes

Reaction equation

HRID 335127 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]([NH:8][C:9]([NH2:11])=[S:10])=[N:6][CH:7]=1.C(N(CC)CC)C.Cl[CH2:27][C:28](=O)[CH3:29].CCO>O>[Br:1][C:2]1[CH:3]=[C:4]([S:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:5]([NH:8][C:9]2[S:10][CH:27]=[C:28]([CH3:29])[N:11]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 866314861-(5-Bromo-3-(phenylthio)pyridin-2-yl)thiourea

Product 1

HCID 247646135-bromo-N-(4-methylthiazol-2-yl)-3-(phenylthio)pyridin-2-amineYield 100.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

mL 1-(5-Bromo-3-(phenylthio)pyridin-2-yl)thiourea (5.0 g, 14.69 mmol), triethylamine (6.0 mL, 44 mmol), 1-chloropropan-2-one (2.3 mL, 29.4 mmol), and EtOH (100 mL) were heated to 70° C. for 6 hours. The ethanol was reduced to ˜½ volume and water (150 mL) added and the precipitate was filtered to afford the title compound (5.6 g, 100% yield) as a tan solid after drying. 1H NMR (CDCl3) δ 9.01 (s, 1H), 8.42 (m, 1H), 7.92 (m, 1H), 7.32-7.15 (m, 5H), 6.44 (m, 1H0, 2.32 (m, 3H). Mass spectrum (apci) m/z=379.8 (M+H).

Workup

  1. additionadded
  2. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-7ef8bc97b5da4a40af7aa29265a582b0
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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