Sodium Hydroxide → HCID 13825455, compound

HRID 1905831Notes

Reaction equation

HRID 1905831 reaction equation
[OH-].[Na+].Cl.[C:4](N)(=[NH:6])[CH3:5].[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[NH:16][CH2:17][C:18]([NH:20][NH2:21])=O>CO.ClCCl>[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[NH:16][CH2:17][C:18]1[N:6]=[C:4]([CH3:5])[NH:21][N:20]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 67170Acetamidine monohydrochlorideHCID 302666STK017412

Product 1

HCID 13825455HCID 13825455, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 8.8 g (0.022 mol) sodium hydroxide in 500 ml methanol was added 20 g (0.22 mol) acetamidine hydrochloride. After stirring for an additional 1/4 hour, 37.7 g (0.2 mol) alpha-(2,6-dimethylphenylamino)acethydrazide was added. The reaction mixture was heated under reflux for about 18 hours, cooled and filtered. The filtrate was evaporated under a reduced pressure to give a solid residue. The residue was diluted with dichloromethane, filtered, dried over magnesium sulfate and evaporated under reduced pressure to give a solid residue, which was triturated with ethyl ether/petroleum ether and dried to give 34.3 g of the product, m.p. 125°-126° C. The product is tabulated in Table I as Compound No. 2-A.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for about 18 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated under a reduced pressure
  6. customto give a solid residue
  7. filtrationfiltered
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure
  10. customto give a solid residue, which
  11. customwas triturated with ethyl ether/petroleum ether
  12. customdried

Sources & evidence

ORD record
ord-d1d2d4bbb79644d4a492a41958a56b38
Source dataset
uspto-grants-1987_03
Patent number
US04648897

Reaction notes

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