Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate → HCID 20353129, compound

HRID 372034Notes

Reaction equation

HRID 372034 reaction equation
C[O-].[Na+].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[CH3:18][NH:19][CH:20]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=1[CH3:30])[CH2:21][NH2:22].[CH3:31][O:32][C:33]([NH:35][C:36](=NC(OC)=O)SC)=[O:34]>C(Cl)(Cl)Cl.O.C(O)(C)C>[CH3:18][N:19]1[CH:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=2[CH3:30])[CH2:21][N:22]=[C:36]1[NH:35][C:33]([O:32][CH3:31])=[O:34]

Participants

8

Reactant 4

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 10942334Sodium MethoxideHCID 20352973HCID 20352973, compound

Product 1

HCID 20353129HCID 20353129, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

This example illustrates methods according to the invention of preparing the dialkyl substituted phenyl compounds of the invention. In this example, 50 ml. of isopropanol and 1.8 g. of sodium methoxide is added to a solution contraining 4.2 g. of the dihydrochloride salt of β-methylamino-β-(2,3-dimethylphenyl)-ethylamine dissolved in 10 ml. of water. The mixture is stirred for 15 minutes and then a solution containing 3.4 g. of a mixture of 1-mono and 1,3-bis(methoxycarbonyl)-S-methylisothiourea in 50 ml. of chloroform is added and then stirred for about two weeks at room temperature. The mixture is then concentrated by evaporation to near dryness and swirled with water, collected, and stirred in 50 ml. of aqueous 1 Normal hydrochloric acid for one hour. The resulting mixture is washed with ethyl ether, then treated with aqueous sodium bicarbonate and filtered. The collected solid is then stirred with distilled water, refiltered and washed in this manner three more times, then dried overnight at room temperature affording a crude product which is then puriified by recrystallization from isopropanol affording 1-methyl-4,5-dihydro-5-(2,3-dimethylphenyl)-2-methoxycarbonylaminoimidazole.

Workup

  1. additiona solution containing 3.4 g
  2. stirringstirred for about two weeks at room temperature
  3. concentrationThe mixture is then concentrated by evaporation
  4. customcollected
  5. stirringstirred in 50 ml
  6. waitof aqueous 1 Normal hydrochloric acid for one hour
  7. washThe resulting mixture is washed with ethyl ether
  8. additiontreated with aqueous sodium bicarbonate
  9. filtrationfiltered
  10. stirringThe collected solid is then stirred with distilled water
  11. washwashed in this manner three more times
  12. customdried overnight at room temperature
  13. customaffording a crude product which
  14. customis then puriified by recrystallization from isopropanol

Sources & evidence

ORD record
ord-92e5c5bfbd5e43eaafe7f5a2e506d18b
Source dataset
uspto-grants-1978_05
Patent number
US04088771

Reaction notes

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