(2-Methylbenzo[D]thiazol-6-YL)methanol → 2-Methyl-1,3-benzothiazole-6-carbaldehyde

HRID 594243Notes

Reaction equation

HRID 594243 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[CH:7][C:5]=2[N:6]=1>C1COCC1.O=[Mn]=O>[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 1

HCID 676590(2-Methylbenzo[D]thiazol-6-YL)methanol

Product 1

HCID 42855972-Methyl-1,3-benzothiazole-6-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2-methylbenzo[d]thiazol-6-yl)methanol (300 mg; 1.67 mmol) in anh. THF (15 ml) was treated with MnO2 (2.269 g; 26.11 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-6-carbaldehyde as a yellow solid. LC-MS (conditions A): tR=0.56 min.; [M+H]+: 178.15 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-66d7553f77c5455185d93199045b1543
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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