Water → HCID 20311737, compound

HRID 2420461Notes

Reaction equation

HRID 2420461 reaction equation
Cl.Cl.[C:3]1([CH:13]([NH:16][CH3:17])[CH2:14][NH2:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.O.C(=O)(O)[O-].[Na+].[CH3:24][O:25][C:26]([NH:28][C:29](=NC(OC)=O)SC)=[O:27]>C(Cl)(Cl)Cl.C(O)(C)C>[CH3:17][N:16]1[CH:13]([C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[CH:5][CH:4]=2)[CH2:14][N:15]=[C:29]1[NH:28][C:26]([O:25][CH3:24])=[O:27]

Participants

7

Reactant 4

HCID 962WaterHCID 98708Methyl [[(methoxycarbonyl)amino](methylthio)methylene]carbamateHCID 516892Sodium BicarbonateHCID 131711214HCID 131711214, compound

Product 1

HCID 20311737HCID 20311737, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

Six grams of 1-(1-naphthyl)-1-methylamino-2-aminoethane, dihydrochloride, prepared in Part A, are stirred into 25 ml of water. Thereafter 35 ml of saturated sodium bicarbonate are added and stirred for several minutes. Then 160 ml of isopropanol followed by 4.16 g of 1,3-bis(methoxycarbonyl)-S-methylisothiourea dissolved in 120 ml of chloroform are added to the mixture. The resulting mixture is stirred under nitrogen for 7 days. The organic solvents are removed in a rotary evaporator and 10% aqueous HCl is added until the pH of the mixture is just acidic. The resulting mixture is extracted with ether and the aqueous mixture is neutralized with saturated sodium bicarbonate, filtered, and pumped dry to give 5.3 g of crude 1-methyl-4,5-dihydro-2-(methoxycarbonylamino)-5-(1-naphthyl)-imidazole, m.p. 187°-190° C. One gram of the crude material is recrystallized from ethanol to give 0.77 g of more pure material, m.p. 194°-197° C.

Workup

  1. additionare added to the mixture
  2. stirringThe resulting mixture is stirred under nitrogen for 7 days
  3. customThe organic solvents are removed in a rotary evaporator and 10% aqueous HCl
  4. additionis added until the pH of the mixture
  5. extractionThe resulting mixture is extracted with ether
  6. filtrationfiltered
  7. custompumped dry

Sources & evidence

ORD record
ord-f1a0bf17fc5643d2ac1a78359aebd940
Source dataset
uspto-grants-1978_08
Patent number
US04110463

Reaction notes

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