2-Thiophenecarboxaldehyde → HCID 58270231, compound

HRID 2272934Notes

Reaction equation

HRID 2272934 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][C:9]([Cl:11])=[CH:8][C:6]=2[N:7]=1.[I-].CC1NC=C[N+]=1C.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH:26]=[O:27].[H-].[Na+]>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([C:26]([C:22]2[S:21][CH:25]=[CH:24][CH:23]=2)=[O:27])[C:5]2[S:10][C:9]([Cl:11])=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 73642-ThiophenecarboxaldehydeHCID 24758Sodium hydrideHCID 22048263HCID 22048263, compoundHCID 87290725HCID 87290725, compound

Product 1

HCID 58270231HCID 58270231, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of Example 3 (6.86 g, 29 mmol) in tetrahydrofuran (200 ml) was treated with dimethylimidazolium iodide (2.13 g, 9.6 mmol), thiophene-2-carbaldehyde (3.19 ml, 35 mmol) and sodium hydride (1.51 g, 38 mmol). The mixture was first stirred at room temperature for 25 min and then heated, with stirring, to 70° C. for 3 h. The reaction mixture was cooled to room temperature and reduced in vacuo. The residue was partitioned between water and dichloromethane. The organic fraction was separated, dried over sodium sulfate and reduced in vacuo. Trituration with methanol gave the title compound in 72% yield, 95% purity. LC-MS m/z=279.1 [M+H]+; RT=3.77 min; LC-MS method 1. 1H NMR: δH (400 MHz, D6-DMSO) 7.40-7.42 (1H, m), 7.95 (1H, s), 8.31 (1H, d, J=4.5 Hz), 8.61 (1H, d, J 4.5 Hz).

Workup

  1. temperatureheated
  2. stirringwith stirring, to 70° C. for 3 h
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe residue was partitioned between water and dichloromethane
  5. customThe organic fraction was separated
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-b3d2e26643e44578b98fc603d681c36b
Source dataset
uspto-grants-2015_09
Patent number
US09120807B2

Reaction notes

Loading…