Sodium → HCID 21180317, compound

HRID 1386939Notes

Reaction equation

HRID 1386939 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[NH:9])=[CH:6][CH:5]=1.[Na].[N:14]([CH2:17][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([NH:23]N)=O)=[N+:15]=[N-:16]>C(O)C>[N:14]([CH2:17][C:18]1[CH:19]=[C:20]([C:21]2[N:10]=[C:8]([C:7]3[CH:11]=[CH:12][C:4]([O:3][CH3:2])=[CH:5][CH:6]=3)[NH:9][N:23]=2)[CH:25]=[CH:26][CH:27]=1)=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 123262194-Methoxybenzamidine HydrochlorideHCID 86757200HCID 86757200, compound

Product 1

HCID 21180317HCID 21180317, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To an ethanolic suspension of 4-methoxybenzamidine hydrochloride salt (1:1) (2.01 g, 10.8 mmol, 1.5 eq.) was added sodium (331 mg, 14.4 mmol, 2 eq.) in ethanol (60 ml), stirring was then continued for 30 min. at r.t. 3-azidomethyl-benzoic acid hydrazide (1.37 g, 7.2 mmol) in ethanol was then added at 20° C. and the mixture heated at reflux for 18 hrs. Upon cooling the product mixture was filtered, the solvent was evaporated and the residue chromatographed over 20 g SiO2 (Merck 230-400 mesh) with CH2Cl2, affording a solid after evaporation of the solvent. The residue was dried under high vacuum overnight at 20° C. affording the title compound (1.25 g, 57% yield) as a white solid. MS: m/e=306 (M+).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 hrs
  3. temperatureUpon cooling the product mixture
  4. filtrationwas filtered
  5. customthe solvent was evaporated
  6. customthe residue chromatographed over 20 g SiO2 (Merck 230-400 mesh) with CH2Cl2
  7. customaffording a solid
  8. customafter evaporation of the solvent
  9. customThe residue was dried under high vacuum overnight at 20° C.

Sources & evidence

ORD record
ord-be98f7bc822b415591b8d1fd5715dee8
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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