Thiourea → HCID 58442508, compound

HRID 1465607Notes

Reaction equation

HRID 1465607 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:6]=1[CH3:13])=O.[NH2:14][C:15]([NH2:17])=[S:16]>CCO>[Cl:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([C:3]2[N:14]=[C:15]([NH2:17])[S:16][CH:2]=2)=[C:6]([CH3:13])[CH:7]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58442377HCID 58442377, compound

Product 1

HCID 58442508HCID 58442508, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-chloro-2,6-dimethylphenyl)ethanone (6.54 g, 25.0 mmol) and thiourea (1.90 g, 25.0 mmol) in 95% EtOH (35.7 mL) was heated at reflux for 60 min. The solution was concentrated and added with water (50 mL) followed by saturated aqueous Na2CO3 (4.0 mL). The resultant precipitate was filtered and recrystallized in toluene (30 mL). The solids were filtered and dried under vacuum to give 4-(4-chloro-2,6-dimethylphenyl)thiazol-2-amine (4.30 g) as white solids in 72% yield: 1H NMR (500 MHz, DMSO-d) δ 7.16 (s, 2 H), 6.43 (s, 1 H), 2.10 (s, 6 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 min
  3. concentrationThe solution was concentrated
  4. additionadded with water (50 mL)
  5. filtrationThe resultant precipitate was filtered
  6. customrecrystallized in toluene (30 mL)
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-d03f89d3f8b24b2fbdb72d48a5a7bb6e
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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