Phosphoric Acid → HCID 178480056, compound

HRID 2396814Notes

Reaction equation

HRID 2396814 reaction equation
[N:1]#[C:2][NH2:3].[CH3:4][C:5]([C:8]1[CH:9]=[C:10]([CH:19]=[C:20]2[N:24]([CH3:25])[C:23](SC)=[N:22][C:21]2=[O:28])[CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])([CH3:7])[CH3:6].CC(C)([O-])C.[K+].P(=O)(O)(O)O>C(O)C.O>[CH3:4][C:5]([C:8]1[CH:9]=[C:10]([CH:19]=[C:20]2[N:24]([CH3:25])[C:23]([NH:3][C:2]#[N:1])=[N:22][C:21]2=[O:28])[CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])([CH3:7])[CH3:6]

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 9864CyanamideHCID 23665647Potassium tert-butoxideHCID 54334135HCID 54334135, compound

Product 1

HCID 178480056HCID 178480056, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Cyanamide (0.2 g, 4.8 mmols) is added to a solution of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1,5-dihydro-1-methyl-2-(methylthio)-4H-imidazol-4-one (1.5 g, 3.9 mmols) and potassium tert-butoxide (0.5 g, 4.3 mmols) in ethanol (25 mL) and the mixture is stirred under an inert atmosphere and heated to reflux. After 2.5 hours the mixture is allowed to cool, and is then poured into water (200 mL), acidified with phosphoric acid, and stirred. After half an hour the product is filtered off, washed three times with water, and dried. Recrystallization from acetonitrile gave the 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4,5-dihydro-1-methyl-4-oxo-1H-imidazol-2-yl-cyanamide (0.7 g), mp 257°-259° C. (dec).

Workup

  1. temperatureheated to reflux
  2. temperatureto cool
  3. stirringstirred
  4. filtrationAfter half an hour the product is filtered off
  5. washwashed three times with water
  6. customdried
  7. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-bc78e5a430b2427dbc70e3faf12df640
Source dataset
uspto-grants-1996_02
Patent number
US05494927

Reaction notes

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