HCID 13075762, compound → N-(alpha-cyanofurfuryl)-3-methylisothiazole-4-carboxylic acid amide

HRID 1030116Notes

Reaction equation

HRID 1030116 reaction equation
Cl.[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH:7]([NH2:10])[C:8]#[N:9].[CH3:11][C:12]1[C:16]([C:17](Cl)=[O:18])=[CH:15][S:14][N:13]=1>N1C=CC=CC=1>[C:8]([CH:7]([NH:10][C:17]([C:16]1[C:12]([CH3:11])=[N:13][S:14][CH:15]=1)=[O:18])[C:3]1[O:2][CH:6]=[CH:5][CH:4]=1)#[N:9]

Participants

4

Reactant 2

HCID 13075762HCID 13075762, compoundHCID 140880593-Methylisothiazole-4-carboxylic acid chloride

Product 1

HCID 14624282N-(alpha-cyanofurfuryl)-3-methylisothiazole-4-carboxylic acid amideYield 71.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.2 g of alpha-(2-furyl)-alpha-aminoacetonitrile hydrochloride was dissolved in 10 ml of pyridine, and with stirring at room temperature, 1.1 g of 3-methylisothiazole-4-carboxylic acid chloride was added dropwise. After the dropwise addition, the mixture was stirred for 1 hour, and distilled under reduced pressure to remove pyridine. The residue was dissolved in ethyl acetate, separated, washed with water, and dried over sodium sulfate The ethyl acetate layer was distilled under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography. Elution with benzene-ethyl acetate gave 1.2 g (yield 70%) of the desired N-(alpha-cyanofurfuryl)-3-methylisothiazole-4-carboxylic acid amide

Workup

  1. additionAfter the dropwise addition
  2. stirringthe mixture was stirred for 1 hour
  3. distillationdistilled under reduced pressure
  4. customto remove pyridine
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. customseparated
  7. washwashed with water
  8. dry with materialdried over sodium sulfate The ethyl acetate layer
  9. distillationwas distilled under reduced pressure
  10. customto remove the solvent
  11. customThe residue was purified by silica gel column chromatography
  12. washElution with benzene-ethyl acetate

Sources & evidence

ORD record
ord-6ff2469719d04814a259dd957b7d64bc
Source dataset
uspto-grants-1992_04
Patent number
US05104886

Reaction notes

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