Cysteamine Hydrochloride → 2-[4-(2-Thienyl)phenyl]-1,3-thiazolane

HRID 250514

反応式

HRID 250514 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.Cl.[NH2:15][CH2:16][CH2:17][SH:18]>CCO.O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:13]=[CH:12][C:9]([CH:10]2[NH:15][CH2:16][CH2:17][S:18]2)=[CH:8][CH:7]=1

参加物

5

反応物 2

HCID 9082Cysteamine HydrochlorideHCID 7364994-(Thiophen-2-yl)benzaldehyde

生成物 1

HCID 114706472-[4-(2-Thienyl)phenyl]-1,3-thiazolane収率 13.6%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 962Water溶媒

実験手順

To a solution of 4-(2-thienyl)benzaldehyde (500.0 mg, 2.66 mmol) in EtOH (5.0 mL) was added a solution of cysteamine HCl (101.0 mg, 0.89 mmol) in water (2.0 mL) dropwise with stirring. The solution was then stirred at room temperature for 18 hours before the bulk of the EtOH was removed by rotary evaporator. The resulting residue was diluted with water (15.0 mL) and extracted with ether (3×30.0 mL) to remove excess aldehyde. The acidic aqueous layer was then basified with the slow addition of solid sodium carbonate (300.0 mg) to afford a white precipitate, which was filtered and washed carefully with water (3×20.0 mL). The solid was dried under reduced pressure to afford 2-[4-(2-thienyl)phenyl]-1,3-thiazolane (15) as a yellow powder (30 mg, 4.6%). 1H nmr (CDCl3, 300 MHz) 3.14, m, H4,4,5; 3.64, m, H5; 5.95, s, H2; 7.08, m, thienyl-H; 7.31, m, 2×thienyl-H; 7.50, d (8.1 Hz), 2×phenyl-H; 7.59, d (8.4 Hz), 2×phenyl-H. ESI (+ve) MS m/z 248 (M+H, 100%).

後処理

  1. customwas removed by rotary evaporator
  2. additionThe resulting residue was diluted with water (15.0 mL)
  3. extractionextracted with ether (3×30.0 mL)
  4. customto remove excess aldehyde
  5. additionThe acidic aqueous layer was then basified with the slow addition of solid sodium carbonate (300.0 mg)
  6. customto afford a white precipitate, which
  7. filtrationwas filtered
  8. washwashed carefully with water (3×20.0 mL)
  9. customThe solid was dried under reduced pressure

出典と根拠

ORDレコード
ord-6709ad7c190f4947a5b051c6fa1d8e1f
出典データセット
uspto-grants-2011_01
特許番号
US07863313B2

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