Thiourea → HCID 86690819, compound

HRID 1465519Notes

Reaction equation

HRID 1465519 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([S:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[Cl:21])=O.[NH2:22][C:23]([NH2:25])=[S:24]>CCO>[Cl:21][C:6]1[CH:7]=[C:8]([S: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 86690820HCID 86690820, compound

Product 1

HCID 86690819HCID 86690819, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(2-chloro-4-(4-methoxyphenylsulfanyl)-6-methylphenyl)ethanone (3-3, 0.127 g) and thiourea (30 mg, 0.33 mmol) in 95% EtOH (3.0 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(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 4-(2-chloro-4-(4-methoxyphenylsulfanyl)-6-methylphenyl)thiazol-2-ylamine (3-4, 70 mg, 0.19 mmol) as yellow solids in 58% yield: 1H NMR (500 MHz, CDCl3) δ 7.44 (m, 2 H), 6.97 (d, J=1.45 Hz, 1 H), 6.93 (m, 3 H), 6.34 (s, 1 H), 3.84 (s, 3 H), 2.13 (s, 3 H); ESI-MS m/z 363.1 (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(s)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c26e2a0ffe9c4ad79cb677f4bc2c5f61
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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