Thiourea → HCID 58442446, compound

HRID 1465599Notes

Reaction equation

HRID 1465599 reaction equation
Br.Br[CH2:3][C:4]([C:6]1[C:7]([CH3:14])=[N:8][C:9]([CH3:13])=[CH:10][C:11]=1[CH3:12])=O.[NH2:15][C:16]([NH2:18])=[S:17]>CCO>[CH3:14][C:7]1[C:6]([C:4]2[N:15]=[C:16]([NH2:18])[S:17][CH:3]=2)=[C:11]([CH3:12])[CH:10]=[C:9]([CH3:13])[N:8]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86657727HCID 86657727, compound

Product 1

HCID 58442446HCID 58442446, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(2,4,6-trimethylpyridin-3-yl)ethanone hydrobromide (9.00 g, 27.9 mmol) and thiourea (2.12 g, 27.9 mmol) in 95% EtOH (39.8 mL) was heated at reflux for 120 min. The solution was concentrated and added with water (50 mL) and saturated aqueous Na2CO3 (5.0 mL). The resultant precipitate was filtered and recrystallized in toluene. The solids were filtered and dried under vacuum to give 4-(2,4,6-trimethylpyridin-3-yl)thiazol-2-amine (3.80 g) as yellow solids in 62% yield: 1H NMR (500 MHz, CDCl3) δ 6.87 (s, 1 H), 6.31 (s, 1 H), 5.07 (s, 2 H), 2.49 (s, 3 H), 2.38 (s, 3 H), 2.14 (s, 3 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 120 min
  3. concentrationThe solution was concentrated
  4. additionadded with water (50 mL) and saturated aqueous Na2CO3 (5.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. customrecrystallized in toluene
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-9d85599148c7408f9362bfc36f7f016b
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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