Thiourea → HCID 86657731, compound

HRID 1465672Notes

Reaction equation

HRID 1465672 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 mixed 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. additionmixed 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-e22e856cc0db4c3597c7b50b503170e4
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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