Thiourea → HCID 58442454, compound

HRID 1465611Notes

Reaction equation

HRID 1465611 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][C:8]([CH:14]([CH3:16])[CH3:15])=[CH:7][C:6]=1[CH:17]([CH3:19])[CH3:18])=O.[NH2:20][C:21]([NH2:23])=[S:22]>CCO>[CH:17]([C:6]1[CH:7]=[C:8]([CH:14]([CH3:16])[CH3:15])[CH:9]=[C:10]([CH:11]([CH3:13])[CH3:12])[C:5]=1[C:3]1[N:20]=[C:21]([NH2:23])[S:22][CH:2]=1)([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 15725271HCID 15725271, compound

Product 1

HCID 58442454HCID 58442454, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(2,4,6-triisopropylphenyl)ethanone (13.9 g, 42.7 mmol) and thiourea (3.24 g, 42.6 mmol) in 95% EtOH (60.9 mL) was heated at reflux overnight. The solution was concentrated and added with water (100 mL), saturated aqueous Na2CO3 (10 mL), and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4(s), and concentrated under reduced pressure, which was purified by column chromatography on silica gel (33% EtOAc in hexanes as eluant) to give 4-(2,4,6-triisopropylphenyl)thiazol-2-amine (3.28 g) as white solids in 25% yield: 1H NMR (500 MHz, CDCl3) δ 7.03 (s, 2 H), 6.22 (s, 1 H), 4.75 (s, 2 H), 2.89 (m, 1 H), 2.68 (m, 2 H), 1.27-1.14 (m, 18H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe solution was concentrated
  4. additionadded with water (100 mL), saturated aqueous Na2CO3 (10 mL)
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous MgSO4(s)
  8. concentrationconcentrated under reduced pressure, which
  9. customwas purified by column chromatography on silica gel (33% EtOAc in hexanes as eluant)

Sources & evidence

ORD record
ord-24e4a46b4a134743ba791896388b94a7
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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