Sodium Sulfite → 6-Benzothiazolecarboxaldehyde, 2-(methylthio)-

HRID 1848083Notes

Reaction equation

HRID 1848083 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([CH2:12][OH:13])[CH:9]=[CH:8][C:6]=2[N:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([CH:12]=[O:13])[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86680995(2-(Methylthio)benzo[d]thiazol-6-yl)methanol

Product 1

HCID 547753816-Benzothiazolecarboxaldehyde, 2-(methylthio)-Yield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of (2-(methylthio)benzo[d]thiazol-6-yl)methanol (958 mg, 4.5 mmol) from Step 3 of Example 36 in CH2Cl2 (20 mL) at 0° C. under argon was added Dess-Martin periodinane (2.0 g, 5.0 mmol) portionwise. The mixture was stirred for 1 h and then diluted with CH2Cl2 (100 mL). To this mixture was added a 50/50 mixture of saturated aq sodium sulfite and saturated aq sodium bicarbonate (40 mL). This mixture was stirred for 10 min and then the CH2Cl2 layer was separated, washed with a saturated aq sodium bicarbonate (50 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 2-(methylthio)benzo[d]thiazole-6-carbaldehyde (937 mg, 99%) as a white solid. LCMS (ESI) m/z 210 (M+H)+.

Workup

  1. additionTo this mixture was added
  2. stirringThis mixture was stirred for 10 min
  3. customthe CH2Cl2 layer was separated
  4. washwashed with a saturated aq sodium bicarbonate (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2e3e9668cccb4f86a65d491f72530dc9
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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