(2-Methylbenzo[d]thiazol-5-yl)methanol → 2-Methylbenzo[d]thiazole-5-carbaldehyde

HRID 594246Notes

Reaction equation

HRID 594246 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][C:5]=2[N:6]=1>C1COCC1.O=[Mn]=O>[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 1

HCID 2341868(2-Methylbenzo[d]thiazol-5-yl)methanol

Product 1

HCID 23088202-Methylbenzo[d]thiazole-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2-methylbenzo[d]thiazol-5-yl)methanol (400 mg; 2.23 mmol) in anh. THF (20 ml) was treated with MnO2 (3.026 g; 34.81 mmol), and the resulting mixture was stirred at rt, under nitrogen, for 6.5 h. The resulting reaction mixture was then filtered over celite, and the separated solids were washed with THF. The filtrate was concentrated to dryness under reduced pressure giving 2-methylbenzo[d]thiazole-5-carbaldehyde as a yellow solid. LC-MS (conditions B): tR=0.70 min.; [M+H]+: 178.03 g/mol.

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas then filtered over celite
  3. washthe separated solids were washed with THF
  4. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b8cc8475964941f1978b92548ae3f5f3
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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