Hexane → 2-(4-Nitrophenyl)thiazole-5-carbaldehyde

HRID 1713047Notes

Reaction equation

HRID 1713047 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([Li])CCC.CCCCCC.[CH:26](N1CCOCC1)=[O:27]>CCOCC>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:11][C:12]([CH:26]=[O:27])=[CH:13][N:14]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8058HexaneHCID 20417N-FormylmorpholineHCID 13546655HCID 13546655, compoundHCID 178418339Butyllithium

Product 1

HCID 152742472-(4-Nitrophenyl)thiazole-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

As depicted in Scheme 25 below, 2-(4-nitrophenyl)thiazole (19.9 mmol) dissolved in ether (20 ml) is added dropwise over 1 hour to a stirred and cooled (−78° C.) solution of butyl lithium (1.5 M) in n-hexane (20 ml, 29.9 mmol), diluted with ether (50 ml). The mixture is stirred at −78° C. for 30 minutes and then a solution of N-formylmorpholine (29.9 mmol) in ether (30 ml) is added dropwise over a time period of 15 minutes. After 30 minutes at −78° C., the mixture is washed with saturated aqueous NaHCO3 (30 ml) and extracted with ether (2×20 ml). The organic phase is dried over Na2SO4 and the solvent is removed under reduced pressure to give the crude 2-(4-Nitro-phenyl)-thiazole-5-carbaldehyde.

Workup

  1. additionis added dropwise over 1 hour to
  2. stirringThe mixture is stirred at −78° C. for 30 minutes
  3. washthe mixture is washed with saturated aqueous NaHCO3 (30 ml)
  4. extractionextracted with ether (2×20 ml)
  5. dry with materialThe organic phase is dried over Na2SO4
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-6f643c6eeeae41dfa3a3e7df05f3ccab
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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