Thiourea → 4-(2-Aminothiazol-4-yl)-3,5-dimethylphenol

HRID 1465524ノート

反応式

HRID 1465524 の反応式
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([OH:12])=[CH:7][C:6]=1[CH3:13])=O.[NH2:14][C:15]([NH2:17])=[S:16]>CCO>[NH2:17][C:15]1[S:16][CH:2]=[C:3]([C:5]2[C:10]([CH3:11])=[CH:9][C:8]([OH:12])=[CH:7][C:6]=2[CH3:13])[N:14]=1

参加物

4

反応物 2

HCID 2723790ThioureaHCID 826327342-Bromo-1-(4-hydroxy-2,6-dimethylphenyl)ethanone

生成物 1

HCID 866908264-(2-Aminothiazol-4-yl)-3,5-dimethylphenol収率 79%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 2-bromo-1-(4-hydroxy-2,6-dimethylphenyl)ethanone (5-1, 2.43 g, 10.0 mmol) and thiourea (1.37 g, 18.0 mmol) in 95% EtOH (30 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 washed with a solution of 50% EtOAc in hexanes. The solids were dried under vacuum to give 4-(2-aminothiazol-4-yl)-3,5-dimethylphenol (5-2, 1.74 g) as pale yellow solids in 79% yield: 1H NMR (500 MHz, CDCl3) δ 8.7 (s, 2 H), 6.17 (s, 2 H), 5.97 (s, 1 H), 1.71 (s, 6 H).

後処理

  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. washwashed with a solution of 50% EtOAc in hexanes
  7. customThe solids were dried under vacuum

出典と根拠

ORDレコード
ord-8b590fbde916412281314a91b3df24c9
出典データセット
uspto-grants-2015_04
特許番号
US08999983B2

反応ノート

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