Pyridine → N-(alpha-cyanofurfuryl)-3-methylisothiazole-5-carboxylic acid amide

HRID 1111404Notes

Reaction equation

HRID 1111404 reaction equation
Cl.[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH:7]([NH2:10])[C:8]#[N:9].[OH-].[Na+].N1C=CC=CC=1.[CH3:19][C:20]1[CH:24]=[C:23]([C:25](Cl)=[O:26])[S:22][N:21]=1>C(OCC)(=O)C>[C:8]([CH:7]([NH:10][C:25]([C:23]1[S:22][N:21]=[C:20]([CH3:19])[CH:24]=1)=[O:26])[C:3]1[O:2][CH:6]=[CH:5][CH:4]=1)#[N:9]

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 13075762HCID 13075762, compoundHCID 151072913-Methyl-1,2-thiazole-5-carbonyl chloride

Product 1

HCID 14624283N-(alpha-cyanofurfuryl)-3-methylisothiazole-5-carboxylic acid amideYield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

5.0 g of alpha-(2-furyl)-alpha-aminoacetonitrile hydrochloride was dehydrochlorinated with sodium hydroxide in ethyl acetate by the same method as in the above Synthesis Example 6. Pyridine (2.5 g) was added, and furthermore, an ethyl acetate solution of 4.0 g of 3-methylisothiazole-5-carboxylic acid chloride was added dropwise After the addition, the mixture was stirred for 1 hour. The reaction mixture was washed with water, dilute hydrochloric acid and a dilute aqueous solution of sodium bicarbonate. Sodium sulfate, and active carbon were added to dehydrate and decolorize the reaction mixture. The solvent was removed under reduced pressure, and the residue was washed with ethyl ether to give 4.5 g (yield 74%) of the desired N-(alpha-cyanofurfuryl)-3-methylisothiazole-5-carboxylic acid amide.

Workup

  1. additionAfter the addition
  2. washThe reaction mixture was washed with water, dilute hydrochloric acid
  3. additionSodium sulfate, and active carbon were added
  4. customThe solvent was removed under reduced pressure
  5. washthe residue was washed with ethyl ether

Sources & evidence

ORD record
ord-6e510778c3e4480aac03312e5548e4b7
Source dataset
uspto-grants-1990_12
Patent number
US04980363

Reaction notes

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