Dimethylformamide → 3-Methoxy-1,2-thiazole-4-carbonitrile

HRID 1862985Notes

Reaction equation

HRID 1862985 reaction equation
Br[C:2]1[C:3]([O:7][CH3:8])=[N:4][S:5][CH:6]=1.[CH3:9][N:10](C)C=O.[C-]#N.[Na+]>O>[C:9]([C:2]1[C:3]([O:7][CH3:8])=[N:4][S:5][CH:6]=1)#[N:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 123939314-Bromo-3-methoxy-1,2-thiazole

Product 1

HCID 123939363-Methoxy-1,2-thiazole-4-carbonitrileYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 38.8 g. (0.2 mole) of 4-bromo-3-methoxyisothiazole prepared as in Example 15 in 80 ml. of dimethylformamide was added 54 g. (0.6 mole) of cuprous cyanide. The mixture was stirred and heated at reflux for 1 hour. Then the reaction mixture was cooled to 25° C., and 40 g. (0.81 mole) of sodium cyanide in 120 ml. of water was added in portions. The mixture exothermed to 60°-70° C. and was allowed again to cool to 25° C. The reaction solution was then extracted thoroughly with ether. The ether extracts were washed with 10% sodium cyanide solution and then water. After drying over anhydrous magnesium sulfate and evaporation 23.4 g. (83%) of 4-cyano-3-methoxyisothiazole was obtained as a white solid, m.p. 60°-62° C. after crystallization from ligroin (90°-120°).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. customexothermed to 60°-70° C.
  4. temperatureto cool to 25° C
  5. extractionThe reaction solution was then extracted thoroughly with ether
  6. washThe ether extracts were washed with 10% sodium cyanide solution
  7. dry with materialAfter drying over anhydrous magnesium sulfate and evaporation 23.4 g

Sources & evidence

ORD record
ord-db86e62ebbcb4849811770125ad487ec
Source dataset
uspto-grants-1979_09
Patent number
US04167575

Reaction notes

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