Triethylamine → N-(alpha-cyanofurfuryl)-2,4-dimethylthiazole-5-carboxylic acid amide

HRID 1030112Notes

Reaction equation

HRID 1030112 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([NH2:9])[C:7]#[N:8].C(N(CC)CC)C.[CH3:17][C:18]1[S:19][C:20]([C:24](Cl)=[O:25])=[C:21]([CH3:23])[N:22]=1.Cl.C(N(CC)CC)C>C(OC(=O)C)C.O>[C:7]([CH:6]([NH:9][C:24]([C:20]1[S:19][C:18]([CH3:17])=[N:22][C:21]=1[CH3:23])=[O:25])[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)#[N:8]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 111477062-Furanacetonitrile, alpha-amino-HCID 146531402,4-Dimethylthiazole-5-carbonyl chloride

Product 1

HCID 14579913N-(alpha-cyanofurfuryl)-2,4-dimethylthiazole-5-carboxylic acid amideYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 120 ml of ethylacetate were dissolved 6.2 g of alpha-(2-furyl)-alpha-aminoacetonitrile and 6.0 g of triethylamine, and with stirring, the 2,4-dimethylthiazole5-carboxylic acid chloride was added dropwise to the solution, and the mixture was stirred at room temperature for 1 hour. Water (150 ml) was added, and the precipitated triethylamine hydrochloride was dissolved. The ethyl acetate layer was separated, washed with water, and dried over sodium sulfate. The dried ethyl acetate layer was distilled under reduced pressure to remove the solvent. The residue was recrystallized from isopropyl ether to give 11.65 g (yield 90.0%) of the desired N-(alpha-cyanofurfuryl)-2,4-dimethylthiazole-5-carboxylic acid amide.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customThe ethyl acetate layer was separated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. distillationThe dried ethyl acetate layer was distilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-eb2400d6d07f40b39555abfe687e9fa6
Source dataset
uspto-grants-1992_04
Patent number
US05104886

Reaction notes

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