Nitrogen → 4-Chloromethyl-thiazole-2-carbaldehyde

HRID 42794

Reaction equation

HRID 42794 reaction equation
N#N.[Cl:3][CH2:4][C:5]1[N:6]=[C:7]([CH2:10][OH:11])[S:8][CH:9]=1>C(C#N)(C)=O.O=[Mn]=O>[Cl:3][CH2:4][C:5]1[N:6]=[C:7]([CH:10]=[O:11])[S:8][CH:9]=1

Participants

5

Reactant 2

HCID 947NitrogenHCID 11073749[4-(Chloromethyl)-1,3-thiazol-2-yl]methanol

Product 1

HCID 552985444-Chloromethyl-thiazole-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 694302-OxopropiononitrileSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of (4-chloromethyl-thiazol-2-yl)-methanol (1.60 g, 9.80 mmol) in AcCN (98.0 mL) was treated at rt with MnO2 (4.73 g, 49.01 mmol). The reaction mixture was stirred at rt overnight before being filtered through Celite and the solvent was removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA) gave the title compound as a colorless oil. TLC:rf (4:1 hept-EA)=0.37. LC-MS-conditions 02: tR=0.77 min.

Workup

  1. filtrationbefore being filtered through Celite
  2. customthe solvent was removed under reduced pressure
  3. customPurification of the residue by FC (4:1 hept-EA)

Sources & evidence

ORD record
ord-7a7c569c4fa34f09b0e58e1a59c58918
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Linked notes

Loading…