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

HRID 335076Notes

Reaction equation

HRID 335076 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-66d48826788245de8658e52969c2258d
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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