Hydrochloric Acid → HCID 10539891, compound

HRID 1289759Notes

Reaction equation

HRID 1289759 reaction equation
[C:1]([NH:4][NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[N:9][CH:8]=1)(=[NH:3])[NH2:2].NC(N)=S.[OH-].[Na+].[CH3:21][N:22]=[C:23]=[S:24].Cl>CS(C)=O>[NH2:2][C:1]1[N:4]([C:23]([NH:22][CH3:21])=[S:24])[N:5]=[C:6]([C:7]2[CH:8]=[N:9][C:10]([Cl:13])=[CH:11][CH:12]=2)[N:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11167Methyl isothiocyanateHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 178513172HCID 178513172, compound

Product 1

HCID 10539891HCID 10539891, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
180 °C

Procedure

The synthesis method of Example 1-(2) was applied. The compound (5.4 g) obtained in (1) above and dimethylsulfoxide (50 ml) were used as reagents and the mixture was stirred at 180° C. for 1 hour. After the reaction, the reaction mixture was ice-cooled and used as it was in the next reaction. The conversion to a thiourea compound was performed according to the method of Example 7-(3). The above-mentioned solution, a 1N aqueous sodium hydroxide solution (20 ml) and methyl isothiocyanate (1.5 g) were used as reagents. After the reaction, the mixture was neutralized with 3N hydrochloric acid and the resulting powder was collected by filtration. The powder was subjected to silica gel column chromatography (chloroform) and recrystallization (chloroform) to give 2.9 g of white crystals (yield 29%).

Workup

  1. customAfter the reaction
  2. temperaturecooled
  3. customwas in the next reaction
  4. customAfter the reaction
  5. filtrationthe resulting powder was collected by filtration
  6. customThe powder was subjected to silica gel column chromatography (chloroform) and recrystallization (chloroform)

Sources & evidence

ORD record
ord-6052e63cbc9b4988bd62b48c4e0631c4
Source dataset
uspto-grants-1998_05
Patent number
US05750545

Reaction notes

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