Dimethylcarbamoyl Chloride → 5-Cyano-2-methylthiazolo[5,4-b]pyridine

HRID 2259522Notes

Reaction equation

HRID 2259522 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:9]([N+:10]=1[O-])=[CH:8][CH:7]=[CH:6][N:5]=2.C[Si]([C:16]#[N:17])(C)C.CN(C)C(Cl)=O.[OH-].[Na+]>C(Cl)Cl>[C:16]([C:6]1[N:5]=[C:4]2[S:3][C:2]([CH3:1])=[N:10][C:9]2=[CH:8][CH:7]=1)#[N:17]

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 14798Sodium HydroxideHCID 82115Trimethylsilyl cyanideHCID 678064122-methylthiazolo[5,4-b]pyridine N-oxide

Product 1

HCID 190029095-Cyano-2-methylthiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Step 3 (4.706 g, 28.3 mmol) in 60 mL of CH2Cl2 was added trimethylsilyl cyanide (7.6 mL, 57 mmol) and the mixture was stirred at room temperature for 30 min. Dimethylcarbamyl chloride (5.2 mL, 56 mmol) was then added and the mixture was heated to reflux overnight. At 0° C., 2N NaOH (60 mL) was added and the mixture was stirred at this temperature one hour. The product was extracted in EtOAc, dried over Na2SO4, and purified by flash chromatography on silica with EtOAc: toluene 10:90; yield: 4.50 g, (91%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. stirringthe mixture was stirred at this temperature one hour
  4. extractionThe product was extracted in EtOAc
  5. dry with materialdried over Na2SO4
  6. custompurified by flash chromatography on silica with EtOAc: toluene 10:90

Sources & evidence

ORD record
ord-f355af3d01064f88a13cb87cbcc2b601
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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