Hydrochloric Acid → HCID 10339510, compound

HRID 1493023Notes

Reaction equation

HRID 1493023 reaction equation
[C:1]([NH:4][NH2:5])([NH2:3])=[NH:2].Cl.C[O-].[Na+].[CH3:10][C:11]([C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:23]=1[O:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])[C:17](OC)=O)([CH3:13])[CH3:12].Cl>CO>[CH3:13][C:11]([C:14]1[CH:15]=[C:16]([C:17]2[NH:5][N:4]=[C:1]([NH2:3])[N:2]=2)[CH:21]=[C:22]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:23]=1[O:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])([CH3:10])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10020919HCID 10020919, compoundHCID 10942334Sodium MethoxideHCID 178418668HCID 178418668, compound

Product 1

HCID 10339510HCID 10339510, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 0° C. slurry of 7.00 g (63.32 mmol) of aminoguanidine hydrochloride in 30 ml of methanol is treated with 3.42 g (63.31 mmol) of sodium methoxide. The mixture is treated dropwise with 5.60 g (15.89 mmol) of 3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]benzoic acid, methyl ester in 20 ml of methanol over 30 minutes under a nitrogen atmosphere. The reaction is warmed at reflux for 40 hours and poured onto 400 ml of ice water. The aqueous mixture is neutralized to pH 7 using 3N HCl. The precipitate is collected and recrystallized from toluene to give 2.79 g (5.98 g theor., 47%) of the product as a white solid, mp 233°-235° C.

Workup

  1. temperatureThe reaction is warmed
  2. temperatureat reflux for 40 hours
  3. customThe precipitate is collected
  4. customrecrystallized from toluene

Sources & evidence

ORD record
ord-3c89ba0980ec4beabfe2a92e1deecaf2
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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