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

HRID 250514Notes

Reaction equation

HRID 250514 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-6709ad7c190f4947a5b051c6fa1d8e1f
Source dataset
uspto-grants-2011_01
Patent number
US07863313B2

Reaction notes

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