Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamate → HCID 135951922, compound

HRID 848107Notes

Reaction equation

HRID 848107 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[NH2:15][CH:16]([C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26])[CH2:17][NH2:18].C(=O)(O)[O-].[Na+].[CH3:32][O:33][C:34]([NH:36][C:37](=NC(OC)=O)SC)=[O:35]>C(O)(C)C.C(Cl)(Cl)Cl>[Cl:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([Cl:25])[C:19]=1[CH:16]1[CH2:17][NH:18][C:37]([NH:36][C:34]([O:33][CH3:32])=[O:35])=[N:15]1

Participants

7

Reactant 4

HCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 516892Sodium BicarbonateHCID 12940480HCID 12940480, compound

Product 1

HCID 135951922HCID 135951922, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

Three and one-half (3.5) grams (g) of the dihydrochloride salt of β-amino-β-(2,6-dichlorophenyl)ethylamine is added to a suitable reaction vessel containing 30 milliliters (ml) of saturated sodium bicarbonate. The resulting mixture is stirred, diluted with 50 mls of isopropanol and a solution of 2.8 g of a mixture of 1-mono- amd 1,3-bis(methoxycarbonyl)-S-methylisothiourea in 50 ml of chloroform is added. Stirring is continued for six days and the solvents are removed under vacuum. The residue is stirred with 70 ml of 2% hydrochloric acid for 30 minutes and the acidic aqueous solution is washed several times with ether, once with toluene and is then treated with excess of saturated sodium bicarbonate. The resulting precipitate is collected by filtration, stirred with water, collected again and dried at 55° under vacuum affording 2.25 g of 4,5-dihydro-4-(2,6-dichlorophenyl)-2-methoxycarbonylaminoimidazole, melting point (mp) 227°-229° C. A small sample is further purified by recrystallization from toluene to give 4,5-dihydro-4-(2,6-dichlorophenyl)-2-methoxycarbonylaminoimidazole, mp 230°-231° C.

Workup

  1. stirringStirring
  2. customthe solvents are removed under vacuum
  3. stirringThe residue is stirred with 70 ml of 2% hydrochloric acid for 30 minutes
  4. washthe acidic aqueous solution is washed several times with ether
  5. additiononce with toluene and is then treated with excess of saturated sodium bicarbonate
  6. filtrationThe resulting precipitate is collected by filtration
  7. stirringstirred with water
  8. customcollected again
  9. customdried at 55° under vacuum

Sources & evidence

ORD record
ord-0d5c1229f6a646ac9e3a770c540a593c
Source dataset
uspto-grants-1981_10
Patent number
US04294844

Reaction notes

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