Thiourea → HCID 86657731, compound

HRID 1843809Notes

Reaction equation

HRID 1843809 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:6]=1[CH3:16])=O.[NH2:17][C:18]([NH2:20])=[S:19]>CCO>[CH3:16][C:6]1[CH:7]=[C:8]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:9]=[C:10]([CH3:11])[C:5]=1[C:3]1[N:17]=[C:18]([NH2:20])[S:19][CH:2]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58442408HCID 58442408, compound

Product 1

HCID 86657731HCID 86657731, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(2,6-dimethyl-4-(methylsulfonyl)phenyl)ethanone (7.60 g, 24.9 mmol) and thiourea (1.90 g, 25.0 mmol) in 95% EtOH (35.6 mL) was heated at reflux for 90 min. The solution was concentrated and added with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL). The resultant precipitate was filtered and recrystallized in toluene (20 mL). The solids were filtered and dried under vacuum to give 4-(2,6-dimethyl-4-(methylsulfonyl)phenyl)thiazol-2-amine (3.28 g) as yellow solids in 47% yield: 1H NMR (500 MHz, CDCl3) δ 7.64 (s, 2 H), 6.34 (s, 1 H), 5.19 (m, 1 H), 3.04 (s, 3 H), 2.26 (s, 6 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 90 min
  3. concentrationThe solution was concentrated
  4. additionadded with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. customrecrystallized in toluene (20 mL)
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-908566a019f54080a4f51eaab3e2d494
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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