Methyl isothiocyanate → 6-[4-(3-methylthioureido)phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

HRID 2290736Notes

Reaction equation

HRID 2290736 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[CH3:16][N:17]=[C:18]=[S:19]>CN(C)C=O>[CH3:16][NH:17][C:18](=[S:19])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 133860336-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

Product 1

HCID 544661276-[4-(3-methylthioureido)phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-oneYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (2 g) and methylisothiocyanate (0.788 g) in dimethylformamide (20 ml) was heated with stirring at 110° C. for 4 hours, followed by after-treatment in the same manner as Example 8 to give 6-[4-(3-methyl-thioureido)phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (2.7 g).

Sources & evidence

ORD record
ord-9bc32f950903457db0ab656fe372931a
Source dataset
uspto-grants-1986_10
Patent number
US04618610

Reaction notes

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