Thiourea → HCID 86690885, compound

HRID 1465583Notes

Reaction equation

HRID 1465583 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[F:21])=O.[NH2:22][C:23]([NH2:25])=[S:24]>CCO>[F:21][C:6]1[CH:7]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:9]=[C:10]([CH3:11])[C:5]=1[C:3]1[N:22]=[C:23]([NH2:25])[S:24][CH:2]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86690886HCID 86690886, compound

Product 1

HCID 86690885HCID 86690885, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(2-fluoro-4-(4-methoxyphenoxy)-6-methylphenyl)ethanone (30-6, 0.60 g) and thiourea (0.160 mg, 2.05 mmol) in 95% EtOH (12.0 mL) was heated at reflux for 60 min. The solution was concentrated under reduced pressure, and the residue was re-dissolved in ethyl acetate. The solution was washed with saturated aqueous NaHCO3, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 4-(2-fluoro-4-(4-methoxyphenoxy)-6-methylphenyl)thiazol-2-ylamine (30-7, 0.450 g, 1.36 mmol) as yellow solids in 80% yield: 1H NMR (500 MHz, CDCl3) δ 6.98 (d, J=9.0 Hz, 2 H), 6.89 (d, J=9.0 Hz, 2 H), 6.60 (s, 1 H), 6.49 (d, J=10.9 Hz, 1 H), 6.41 (s, 0.1 H), 3.80 (d, J=3.4 Hz, 3 H), 2.26 (s, 3H). ESI-MS: m/z 331.0 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 min
  3. concentrationThe solution was concentrated under reduced pressure
  4. dissolutionthe residue was re-dissolved in ethyl acetate
  5. washThe solution was washed with saturated aqueous NaHCO3
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0c5d07a134694c95bf2e867939b18271
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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