Thiourea → HCID 86690863, compound

HRID 1465560Notes

Reaction equation

HRID 1465560 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][N:14]=2)=[CH:7][C:6]=1[CH3:21])=O.[NH2:22][C:23]([NH2:25])=[S:24]>CCO>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:8]2[CH:9]=[C:10]([CH3:11])[C:5]([C:3]3[N:22]=[C:23]([NH2:25])[S:24][CH:2]=3)=[C:6]([CH3:21])[CH:7]=2)=[N:14][CH:15]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 866908642-Bromo-1-{4-((5-methoxypyridin-2-yl)oxy)-2,6-dimethylphenyl}ethanone

Product 1

HCID 86690863HCID 86690863, compoundYield 5.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-{4-((5-methoxypyridin-2-yl)oxy)-2,6-dimethylphenyl}ethanone (18-3, 1.89 g, 5.40 mmol) and thiourea (0.47 g, 6.18 mmol) in 95% EtOH (20.0 mL) was heated at reflux for 2.0 h. The solution was concentrated and added with water (10 mL) and saturated aqueous Na2CO3 (1.0 mL). The resultant precipitate was filtered and washed with hot water. The solids were filtered and dried under vacuum to give 4-{4-((5-methoxypyridin-2-yl)oxy)-2,6-dimethylphenyl}thiazol-2-amine (18-4, 0.10 g) as yellow solids in 5.7% yield: 1H NMR (500 MHz, CDCl3) δ 7.60 (m, 1 H), 7.30 (m, 1 H), 6.89 (m, 1 H), 6.77 (s, 2 H), 6.25 (s, 1 H), 3.83 (s, 3 H), 2.17 (s, 6 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.0 h
  3. concentrationThe solution was concentrated
  4. additionadded with water (10 mL) and saturated aqueous Na2CO3 (1.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. washwashed with hot water
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-985787765d284381bea8bdaa7117bb39
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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