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

HRID 250514노트

반응식

HRID 250514 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-6709ad7c190f4947a5b051c6fa1d8e1f
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863313B2

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