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

HRID 1111402Notes

Reaction equation

HRID 1111402 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8]([OH:10])=O)=[C:5]([CH3:7])[N:6]=1.C(N(CC)CC)C.ClC(OCCCC)=O.Cl.[O:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH:32]([NH2:35])[C:33]#[N:34]>O1CCCC1>[C:33]([CH:32]([NH:35][C:8]([C:4]1[S:3][C:2]([CH3:1])=[N:6][C:5]=1[CH3:7])=[O:10])[C:28]1[O:27][CH:31]=[CH:30][CH:29]=1)#[N:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 61140Butyl chloroformateHCID 736488Dimethyl-1,3-thiazole-5-carboxylic acidHCID 13075762HCID 13075762, compound

Product 1

HCID 14579913N-(alpha-cyanofurfuryl)-2,4-dimethylthiazole-5-carboxylic acid amideYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.71 g of 2,4-dimethylthiazole-5-carboxylic acid was suspended in 70 ml of tetrahydrofuran, and 6.67 g of triethylamine was added. The mixture was stirred. While it was cooled to -10° to -5° C., 4.10 g of n-butyl chloroformate was added, and the mixture was stirred at this temperature for 30 minutes, and then 4.03 g of alpha-(2-furyl)-alpha-aminoacetonitrile hydrochloride was added. The mixture was stirred at room temperature for 5 hours, and then left to stand overnight. The precipitate was separated by filtration and distilled under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography. Elution with hexane/ethyl acetate gave 4.20 g (yield 53.6%) of the desired N-(alpha-cyanofurfuryl)-2,4-dimethylthiazole-5-carboxylic acid amide.

Workup

  1. temperatureWhile it was cooled to -10° to -5° C.
  2. stirringthe mixture was stirred at this temperature for 30 minutes
  3. stirringThe mixture was stirred at room temperature for 5 hours
  4. waitleft
  5. customThe precipitate was separated by filtration
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by silica gel column chromatography
  9. washElution with hexane/ethyl acetate

Sources & evidence

ORD record
ord-1a2c2fc7423347f5b2da08d284023eb1
Source dataset
uspto-grants-1990_12
Patent number
US04980363

Reaction notes

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