Triethylamine → HCID 14624273, compound

HRID 1111401Notes

Reaction equation

HRID 1111401 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.[CH2:17]([C:19]1[S:20][C:21]([C:26](Cl)=[O:27])=[C:22]([CH2:24][CH3:25])[N:23]=1)[CH3:18].Cl.C(N(CC)CC)C>C(OCC)(=O)C.O>[C:7]([CH:6]([NH:9][C:26]([C:21]1[S:20][C:19]([CH2:17][CH3:18])=[N:23][C:22]=1[CH2:24][CH3:25])=[O:27])[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 15107290HCID 15107290, compound

Product 1

HCID 14624273HCID 14624273, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.80 g of alpha-(2-furyl)-alpha-aminoacetonitrile and 6.0 g of triethylamine were dissolved in 50 ml of ethyl acetate, and with stirring, 2.1 g of the 2,4-diethylthiazole-5-carboxylic acid chloride was added dropwise, 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 evaporated under reduced pressure to remove the solvent. The residue was recrystallized from n-hexane to give 2.41 g (yield 80.0%) 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. customThe dried ethyl acetate layer was evaporated under reduced pressure
  6. customto remove the solvent
  7. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-56e9a72b40954118943b559787322d84
Source dataset
uspto-grants-1990_12
Patent number
US04980363

Reaction notes

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