Cyanamide → HCID 178440787, compound

HRID 486103Notes

Reaction equation

HRID 486103 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-33320cda9837429da1c83fb86afa9e4b
Source dataset
uspto-grants-1994_03
Patent number
US05290800

Reaction notes

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