Guanidine Hydrochloride → HCID 178440701, compound

HRID 1657082Notes

Reaction equation

HRID 1657082 reaction equation
[Na].Cl.[NH2:3][C:4]([NH2:6])=[NH:5].CC(C)([O-])C.[Na+].[CH3:13][C:14]([C:17]1[CH:22]=[C:21]([C:23]2[O:24][C:25](S(C)(=O)=O)=[N:26][N:27]=2)[CH:20]=[C:19]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:18]=1[OH:36])([CH3:16])[CH3:15]>C(O)(C)(C)C>[CH3:16][C:14]([C:17]1[CH:22]=[C:21]([C:23]2[O:24][C:25]([NH:5][C:4]([NH2:6])=[NH:3])=[N:26][N:27]=2)[CH:20]=[C:19]([C:32]([CH3:33])([CH3:34])[CH3:35])[C:18]=1[OH:36])([CH3:13])[CH3:15]

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 5360545SodiumHCID 23676156Sodium t-butoxideHCID 136403400HCID 136403400, compound

Product 1

HCID 178440701HCID 178440701, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Sodium (0.68 g, 29.7 mmol) is dissolved in 40 ml of t-butanol under N2 atmosphere. Guanidine hydrochloride (3.31 g, 34.65 mmol) is added to the sodium t-butoxide solution and stirred at room temperature for 0.5 hour. 2,6-Bis(1,1-dimethylethyl)-4-[5-(methylsulfonyl)-1,3,4-oxadiazole-2-yl]-phenol (3.50 g, 9.93 mmol) is added and the reaction is warmed at reflux overnight. The cool reaction mixture is concentrated in vacuo and is recrystallized from methanol-water. The solid is dissolved in diethyl ether and treated with ethereal HCl and the precipitate is collected and recrystallized from ethanol-ether to give 1.53 g (3.29 g theor., 46%) of N-[5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-oxadiazole-2-yl]-guanidine, monochloride as a white solid: mp 223°-224° C.

Workup

  1. temperaturethe reaction is warmed
  2. temperatureat reflux overnight
  3. customThe cool reaction mixture
  4. concentrationis concentrated in vacuo
  5. customis recrystallized from methanol-water
  6. dissolutionThe solid is dissolved in diethyl ether
  7. additiontreated with ethereal HCl
  8. customthe precipitate is collected
  9. customrecrystallized from ethanol-ether

Sources & evidence

ORD record
ord-2ea278a0081c4ad1b36b7311665d2a77
Source dataset
uspto-grants-1993_10
Patent number
US05256680

Reaction notes

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