Nitrogen → 4-Chloromethyl-thiazole-2-carbaldehyde

HRID 2065034Notes

Reaction equation

HRID 2065034 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-f0047d27b7b044e28bb2e54ee7ca50c5
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

Loading…