Chloroacetone → 5-chloro-N-(4-methylthiazol-2-yl)-3-phenoxypyridin-2-amine

HRID 1806009Notes

Reaction equation

HRID 1806009 reaction equation
Cl[CH2:2][C:3](=O)[CH3:4].[Cl:6][C:7]1[CH:8]=[C:9]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10]([NH:13][C:14]([NH2:16])=[S:15])=[N:11][CH:12]=1.C(N(CC)CC)C>C(O)C>[Cl:6][C:7]1[CH:8]=[C:9]([O:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:10]([NH:13][C:14]2[S:15][CH:2]=[C:3]([CH3:4])[N:16]=2)=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 866314681-(5-Chloro-3-phenoxypyridin-2-yl)thiourea

Product 1

HCID 247655385-chloro-N-(4-methylthiazol-2-yl)-3-phenoxypyridin-2-amineYield 88.96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-chloropropan-2-one (3.827 g, 41.36 mmol), 1-(5-chloro-3-phenoxypyridin-2-yl)thiourea (8.265 g, 29.54 mmol), triethylamine (7.001 mL, 50.23 mmol), and ethanol (30 mL) was refluxed for 3 hours. The ethanol was removed to about one third original volume, and then the reaction mixture was cooled in an ice bath and filtered. The solids were washed with cold ethanol and dried to afford the title compound (8.35 g, 88.96% yield) as a light yellow powder. 1H NMR (d6-DMSO) δ 10.94 (bs, 1H), 8.15 (d, 1H), 7.43 (t, 2H), 7.32 (d, 1H), 7.20 (t, 1H), 7.19 (d, 2H), 6.60 (s, 1H), 2.23 (s, 3H); Mass spectrum (apci) m/z=318.2 (M+H).

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe ethanol was removed to about one third original volume
  3. temperaturethe reaction mixture was cooled in an ice bath
  4. filtrationfiltered
  5. washThe solids were washed with cold ethanol
  6. customdried

Sources & evidence

ORD record
ord-82e6c00f65c842aa8233a505a59b42d0
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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