Thiourea → HCID 58442442, compound

HRID 1843769Notes

Reaction equation

HRID 1843769 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][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:7][C:6]=1[CH3:21])=O.[NH2:22][C:23]([NH2:25])=[S:24]>CCO>[CH3:20][O:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[O:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([C:3]2[N:22]=[C:23]([NH2:25])[S:24][CH:2]=2)=[C:6]([CH3:21])[CH:7]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58442432HCID 58442432, compound

Product 1

HCID 58442442HCID 58442442, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-(3-methoxyphenoxy)-2,6-dimethylphenyl)ethanone (6.98 g, 20.0 mmol) and thiourea (1.52 g, 20.0 mmol) in 95% EtOH (28.5 mL) was heated at reflux for 5.0 h. The solution was concentrated and added with water (50 mL) and saturated aqueous Na2CO3 (1.0 mL), and extracted with ethyl acetate (100 ml). The organic layer was washed with brine, dried over anhydrous MgSO4(s), and concentrated under reduced pressure to give 4-(4-(3-methoxyphenoxy)-2,6-dimethylphenyl)thiazol-2-amine (4.30 g) as deep-brown oil, which was used directly for the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5.0 h
  3. concentrationThe solution was concentrated
  4. additionadded with water (50 mL) and saturated aqueous Na2CO3 (1.0 mL)
  5. extractionextracted with ethyl acetate (100 ml)
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous MgSO4(s)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b2237b1409b4b2fa34cd0ba0643aa7a
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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