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

HRID 1111399Notes

Reaction equation

HRID 1111399 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-dimethylthiazole-5-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 The dried ethyl acetate layer
  5. distillationwas distilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-7f2ce2df6a7d4959bef89ea9743329d7
Source dataset
uspto-grants-1990_12
Patent number
US04980363

Reaction notes

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