Hydrochloric Acid → HCID 20353069, compound

HRID 372033Notes

Reaction equation

HRID 372033 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[CH3:15][NH:16][CH:17]([C:20]1[CH:25]=[CH:24][C:23]2[O:26][CH2:27][O:28][C:22]=2[CH:21]=1)[CH2:18][NH2:19].C[O-].[Na+].[CH3:32][O:33][C:34]([NH:36][C:37](=NC(OC)=O)SC)=[O:35].Cl>C(Cl)(Cl)Cl.C(O)(C)C.O>[CH3:15][N:16]1[CH:17]([C:20]2[CH:25]=[CH:24][C:23]3[O:26][CH2:27][O:28][C:22]=3[CH:21]=2)[CH2:18][N:19]=[C:37]1[NH:36][C:34]([O:33][CH3:32])=[O:35]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 10942334Sodium MethoxideHCID 20353018HCID 20353018, compound

Product 1

HCID 20353069HCID 20353069, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

This example illustrates methods according to the invention of preparing the methylenedioxy substituted phenyl compounds of the invention. In this example 9.0 g. of the dihydrochloride salt of β-methylamino-β-(3,4-methylenedioxyphenyl)-ethylamine is dissolved in 40 ml. of water. This solution is stirred and added successively to it is 150 ml. of isopropanol, 4.1 g. of sodium methoxide and finally 8 g. of a mixture of 1-mono and 1,3-bis(methoxycarbonyl)-S-methylisothiourea in 100 ml. of chloroform. The mixture is then stirred for 12 days at room temperature. It is then concentrated under vacuum affording a gummy residue which is then incompletely dissolved in 100 ml. of approximately 1N aqueous hydrochloric acid. The resulting mixture is first filtered and then washed with ethyl ether, heated with charcoal and filtered again. The crude product is then precipitated from the filtrate by addition of aqueous sodium bicarbonate. The precipitate is collected by filtration, stirred with distilled water, collected again and then dried under vacuum affording crude of 1-methyl-4,5-dihydro-5-(3,4-methylenedioxyphenyl)-2-methoxycarbonylaminoimidazole which is recrystallized from isopropanol yielding the purified product. A hydrogen-ion addition salt may be prepared according to the methods set forth in part A of Examples 1-3.

Workup

  1. additionadded successively to it
  2. stirringThe mixture is then stirred for 12 days at room temperature
  3. concentrationIt is then concentrated under vacuum
  4. customaffording a gummy residue which
  5. dissolutionis then incompletely dissolved in 100 ml
  6. filtrationThe resulting mixture is first filtered
  7. washwashed with ethyl ether
  8. temperatureheated with charcoal
  9. filtrationfiltered again
  10. customThe crude product is then precipitated from the filtrate by addition of aqueous sodium bicarbonate
  11. filtrationThe precipitate is collected by filtration
  12. stirringstirred with distilled water
  13. customcollected again
  14. customdried under vacuum

Sources & evidence

ORD record
ord-e6e870fb41ca4723bc6d7770d5d78c17
Source dataset
uspto-grants-1978_05
Patent number
US04088771

Reaction notes

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