Ethyl Acetate → HCID 54315344, compound

HRID 1111405Notes

Reaction equation

HRID 1111405 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8](O)=O)=[C:5](C)[N:6]=1.S(Cl)(Cl)=O.[NH2:15][CH2:16][C:17]#[N:18].S(O)(O)(=O)=O.N[CH2:25]C#N.[OH-].[Na+].C([O:33][CH2:34][CH3:35])(=O)C>O.C(N(CC)CC)C.C1(C)C=CC=CC=1.CN(C)C=O>[C:17]([CH2:16][NH:15][C:34]([C:35]1[S:3][C:2]([CH2:1][CH3:25])=[N:6][C:5]=1[CH2:4][CH3:8])=[O:33])#[N:18]

Participants

11

Reactant 6

HCID 8857Ethyl Acetate2×HCID 10901AminoacetonitrileHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 196971Aminoacetonitrile sulfate (1:1)HCID 736488Dimethyl-1,3-thiazole-5-carboxylic acid

Product 1

HCID 54315344HCID 54315344, compoundYield 53%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 10 g of 2,4-dimethylthiazole-5-carboxylic acid, 13.6 g of thionyl chloride and 70 ml of toluene was cooled with ice, and with stirring, 8.4 g of N,N-dimethylformamide was added. The mixture was stirred for 3 hours at 3° to 5° C. and then for 1 hour at 20° C., and 200 ml of toluene and 37 g of triethylamine were added. An ethyl acetate solution of aminoacetonitrile prepared from aminoacetonitrile sulfate using ethyl acetate and NaOH was gradually added to the reaction mixture being cooled with ice. The mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried, and distilled under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography. Elution with hexane/ethyl acetate gave 6.6 g (yield 53%) of N-cyanomethyl-2,4-diethylthiazole-5-carboxylic acid amide.

Workup

  1. temperaturewas cooled with ice
  2. stirringThe mixture was stirred for 3 hours at 3° to 5° C.
  3. additionwas gradually added to the reaction mixture
  4. temperaturebeing cooled with ice
  5. stirringThe mixture was stirred at room temperature for 1 hour
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with water
  8. customdried
  9. distillationdistilled under reduced pressure
  10. customto remove the solvent
  11. customThe residue was purified by silica gel column chromatography
  12. washElution with hexane/ethyl acetate

Sources & evidence

ORD record
ord-e7f1771623a14cca899b5852bf36f824
Source dataset
uspto-grants-1990_12
Patent number
US04980363

Reaction notes

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