Guanidine → HCID 135503589, compound

HRID 1493026Notes

Reaction equation

HRID 1493026 reaction equation
N[C:2]([NH2:4])=[NH:3].[CH3:5][C:6]([C:9]1[CH:10]=[C:11]([C:20](Cl)=[N:21][OH:22])[CH:12]=[C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:14]=1[OH:15])([CH3:8])[CH3:7]>C(O)C>[NH2:4][C:2]1[O:22][N:21]=[C:20]([C:11]2[CH:12]=[C:13]([C:16]([CH3:17])([CH3:18])[CH3:19])[C:14]([OH:15])=[C:9]([C:6]([CH3:8])([CH3:7])[CH3:5])[CH:10]=2)[N:3]=1

Participants

4

Reactant 2

HCID 3520GuanidineHCID 136401346HCID 136401346, compound

Product 1

HCID 135503589HCID 135503589, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 2.6 g (0.044 mole) of guanidine in absolute ethanol (100 ml) is added dropwise a solution of 6.2 g (0.022 mole) of 3,5-bis(1,1-dimethylethyl)-N,4-dihydroxybenzenecarboximidoyl chloride in absolute ethanol (60 ml). The mixture is stirred at room temperature for 18 hours, then evaporated to dryness (vacuum). The oil is dissolved in ethyl acetate (125 ml) and poured into water (125 ml). While stirring, the solution is acidified (pH 4.0-5.0) with 1N hydrochloric acid. The organic layer is separated, washed with water (2×100 ml), and dried (anhydrous magnesium sulfate). Evaporation of the organic layer leaves 5.0 g of crude material. Purification by flash chromatography (silica gel, ethyl acetate/hexane elution) gives 1.0 g (16%) of analytically pure 4-(5-amino-1,2,4-oxadiazol-3-yl)-2,6-bis(1,1-dimethylethyl)phenol, mp 202°-204° C.

Workup

  1. customevaporated to dryness (vacuum)
  2. dissolutionThe oil is dissolved in ethyl acetate (125 ml)
  3. additionpoured into water (125 ml)
  4. stirringWhile stirring
  5. customThe organic layer is separated
  6. washwashed with water (2×100 ml)
  7. dry with materialdried (anhydrous magnesium sulfate)
  8. customEvaporation of the organic layer
  9. customleaves 5.0 g of crude material
  10. customPurification
  11. washby flash chromatography (silica gel, ethyl acetate/hexane elution)

Sources & evidence

ORD record
ord-48820f8ad23342538925486e73297475
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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