Dimethylformamide dimethyl acetal → 1-(2',6'-Dimethylphenyl)-4-amino-1,2-dihydro-1,3,5-triazin-2-one

HRID 28056Notes

Reaction equation

HRID 28056 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[NH:10][C:11]([NH:13][C:14]([NH2:16])=O)=N.C[O:18][CH:19](OC)[N:20](C)C>CC#N>[CH3:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH3:2])[C:4]=1[N:10]1[CH:11]=[N:13][C:14]([NH2:16])=[N:20][C:19]1=[O:18]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178424809HCID 178424809, compound

Product 1

HCID 130393641-(2',6'-Dimethylphenyl)-4-amino-1,2-dihydro-1,3,5-triazin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a magnetically stirred suspension of 9.7 g. (40 mmol) of 1-(2',6'-dimethylphenyl)amidinourea hydrochloride in 50 ml. of CH3CN at room temperature is added 5.7 g. (48 mmol) of N,N-dimethylformamide dimethylacetal. The reaction mixture is stirred for 10 minutes after which all of the solid material goes into solution. The solution is stirred for 5 minutes after which a seed crystal is added. A white solid precipitates. The reaction mixture is stirred for an additional 1.5 hours, after which the solid precipitate is filtered to yield 1-(2',6' -dimethylphenyl)-4-amino-1,2-dihydro-1,3,5-triazin-2-one, melting point 248.5°-249.5° C. When recrystallized from absolute EtOH the product is obtained as a white solid with melting point 258.6°-259° C.

Workup

  1. additionTo a magnetically stirred suspension of 9.7 g
  2. stirringThe solution is stirred for 5 minutes after which a seed crystal
  3. additionis added
  4. customA white solid precipitates
  5. stirringThe reaction mixture is stirred for an additional 1.5 hours
  6. filtrationafter which the solid precipitate is filtered

Sources & evidence

ORD record
ord-36ed6eb87518425c89cf74c419cbd33e
Source dataset
uspto-grants-1980_09
Patent number
US04225315

Reaction notes

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