Dimethylformamide → 1,3-Benzothiazole-2-carbaldehyde

HRID 868925Notes

Reaction equation

HRID 868925 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Li]CCCC.CN([CH:18]=[O:19])C>>[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

4

Reactant 3

HCID 6228DimethylformamideHCID 7222BenzothiazoleHCID 178418339Butyllithium

Product 1

HCID 2416081,3-Benzothiazole-2-carbaldehyde

Procedure

To a solution of benzo[d]thiazole (1 g, 7 mmol) in DMF (10 mL) was added n-BuLi (8.4 mL, 21 mmol) over 15 min at −78° C. and the mixture was stirred at this temperature for 1 hour. The reaction was quenched with water, extracted with EtOAc and dried over anhydrous sodium sulfate. The solution was then concentrated under vacuum to give benzo[d]thiazole-2-carbaldehyde as a light yellow solid (500 mg).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe solution was then concentrated under vacuum

Sources & evidence

ORD record
ord-ef142b27efd94868bf43a9dee085e6d1
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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