Thiourea → HCID 86690811, compound

HRID 1465512Notes

Reaction equation

HRID 1465512 reaction equation
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([N:12]([CH3:14])[CH3:13])=[CH:7][C:6]=1[CH3:15])=O.[NH2:16][C:17]([NH2:19])=[S:18]>CCO>[CH3:13][N:12]([CH3:14])[C:8]1[CH:9]=[C:10]([CH3:11])[C:5]([C:3]2[N:16]=[C:17]([NH2:19])[S:18][CH:2]=2)=[C:6]([CH3:15])[CH:7]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86690812HCID 86690812, compound

Product 1

HCID 86690811HCID 86690811, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-1-(4-(dimethylamino)-2,6-dimethylphenyl)ethanone (1-3, 0.900 g, 3.33 mmol) and thiourea (0.250 g, 3.33 mmol) in 95% EtOH (4.8 mL) was heated at reflux for 60 min. The solution was concentrated and added with water (30 mL) and saturated aqueous Na2CO3 (1.0 mL). The resultant precipitate was filtered and purified by flash column chromatography on silica gel to give 4-(4-(dimethylamino)-2,6-dimethylphenyl)thiazol-2-amine (1-4, 0.50 g) as brown solids in 61% yield: 1H NMR (500 MHz, CDCl3) δ 6.45 (s, 2 H), 6.25 (s, 1 H), 4.90 (bs, 2 H), 2.93 (s, 6 H), 2.15 (s, 6 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 min
  3. concentrationThe solution was concentrated
  4. additionadded with water (30 mL) and saturated aqueous Na2CO3 (1.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-3de44010859743f6aeb728d640356054
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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