Cyanamide → HCID 178440787, compound

HRID 2396809Notes

Reaction equation

HRID 2396809 reaction equation
[N:1]#[C:2][NH2:3].CC(C)([O-])C.[K+].[CH3:10][C:11]([C:14]1[CH:15]=[C:16]([CH:25]=[C:26]2[O:30][C:29](SC)=[N:28][C:27]2=[O:33])[CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])([CH3:13])[CH3:12]>C(O)C>[CH3:10][C:11]([C:14]1[CH:15]=[C:16]([CH:25]=[C:26]2[O:30][C:29]([NH:3][C:2]#[N:1])=[N:28][C:27]2=[O:33])[CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 9864CyanamideHCID 23665647Potassium tert-butoxideHCID 54084465HCID 54084465, compound

Product 1

HCID 178440787HCID 178440787, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension of 0.38 g (0.0090 mole) of cyanamide in 50 mL of ethanol is cooled in ice and treated in small portions with 0.93 g (0.0083 mole) of potassium tert-butoxide. After stirring for 15 minutes, 2.6 g (0.0075 mole) of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-(methylthio)-4(5H)-oxazolone is added, followed by an additional 25 mL of ethanol. The mixture is stirred at reflux for 3 hours, then cooled to allow precipitation of the potassium salt of the product. The salt is filtered, washed several times with ether, suspended in 100 mL of cold water, and acidified with 1.0 mL of acetic acid. The mixture is stirred for 30 minutes and extracted with ethyl acetate (4×75 mL). The combined organic layers are washed with brine (2×150 mL), dried (anhydrous sodium sulfate), and evaporated to yield 1.0 g (38%) of the nitrile product, [5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4,5-dihydro-4-oxo-2-oxazolyl]cyanamide. A sample recrystallized from hexane:ethyl acetate had mp 220° C. dec.

Workup

  1. temperatureis cooled in ice
  2. stirringThe mixture is stirred
  3. temperatureat reflux for 3 hours
  4. temperaturecooled
  5. customprecipitation of the potassium salt of the product
  6. filtrationThe salt is filtered
  7. washwashed several times with ether
  8. stirringThe mixture is stirred for 30 minutes
  9. extractionextracted with ethyl acetate (4×75 mL)
  10. washThe combined organic layers are washed with brine (2×150 mL)
  11. dry with materialdried (anhydrous sodium sulfate)
  12. customevaporated

Sources & evidence

ORD record
ord-f44c3fc6b8c44794808cc543d627c3ea
Source dataset
uspto-grants-1996_02
Patent number
US05494927

Reaction notes

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