Triethylamine → HCID 18507280, compound

HRID 1356093Notes

Reaction equation

HRID 1356093 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8](=[C:11]([S:14][CH3:15])SC)[C:9]#[N:10])=O.N[N:17]=[CH:18][NH:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([N:30](CC)CC)C>CN(C=O)C>[C:9]([C:8]1[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[N:17][C:18]([NH:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:30][C:11]=1[S:14][CH3:15])#[N:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28190932-(furan-2-carbonyl)-3,3-bis-methylsulfanyl-acrylonitrileHCID 136401065HCID 136401065, compound

Product 1

HCID 18507280HCID 18507280, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the method of Rudorf and Augustin (J. Prakt. Chem. 1978, 320, 576), a solution of 250 mg (1.04 mmol) 2-(furan-2-carbonyl)-3,3-bis-methylsulfanyl-acrylonitrile, 205 mg (1.25 mmol) N-(aminoiminomethyl)benzamide and 0.36 ml (2.61 mmol) triethylamine in 5 ml DMF was heated at reflux for 6 h. The reaction mixture was then cooled to room temperature and partitioned between ethyl acetate and water. The phases were separated and the organic phase dried over sodium sulfate and concentrated in vacuo. Chromatography (hexane then ethyl acetate/hexane 1/1) afforded 199 mg (57%) N-(5-cyano-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-yl)-benzamide as an off-white amorphous solid. ES-MS m/e (%): 359 (M+Na+, 36), 337 (M+H+, 100).

Workup

  1. temperatureat reflux for 6 h
  2. custompartitioned between ethyl acetate and water
  3. customThe phases were separated
  4. dry with materialthe organic phase dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5f71ee8964d4fc19a24ed2f4c42395f
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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