Dimethylformamide → 1,3-Benzothiazole-2-carbaldehyde

HRID 1860386Notes

Reaction equation

HRID 1860386 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C([Li])CCC.CN([CH:18]=[O:19])C>C1COCC1.CCCCCC>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:18]=[O:19]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 7222BenzothiazoleHCID 178418339Butyllithium

Product 1

HCID 2416081,3-Benzothiazole-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a stirred solution of benzothiazole (3.28 ml) in anydrous THF (40 ml), at −78°, under a nitrogen atmosphere, butyllithium (2.0 ml of a 1.6M solution in hexane) was added dropwise. After 0.33 h, a solution of DMF (7 ml) in anydrous THF (20 ml) was added dropwise and the reaction mixture was allowed to rise to 0° over 1 h. The reaction was quenched by pouring the mixture into water (100 ml) and extracted with EE (2×150 ml). The organic layer was washed with brine, dried and the solvent evaporated under reduced pressure. The crude residue was purified by flash chromatography (eluting with CH-EA in gradient from 95:5 to 8:2), and crystallized from PE to give the title compound as a yellow solid (1.88 g). M.p. 76-77°

Workup

  1. waitto rise to 0° over 1 h
  2. customThe reaction was quenched
  3. additionby pouring the mixture into water (100 ml)
  4. extractionextracted with EE (2×150 ml)
  5. washThe organic layer was washed with brine
  6. customdried
  7. customthe solvent evaporated under reduced pressure
  8. customThe crude residue was purified by flash chromatography (eluting with CH-EA in gradient from 95:5 to 8:2)
  9. customcrystallized from PE

Sources & evidence

ORD record
ord-bfd6ad37301847daaf34430becb5801d
Source dataset
uspto-grants-2003_03
Patent number
US06531466B2

Reaction notes

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