Formaldehyde → 1-Hydroxymethyl-3,5-dimethyl-1,2,4-triazole

HRID 614702Notes

Reaction equation

HRID 614702 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[NH:4][N:3]=1.C=O.S(Cl)(Cl)=O.ClCN1C(C)=NC(C)=N1.[OH:23][C:24]1C2C(=CC=CC=2)C(O)=CC=1C(NCCCOC1C=CC(C(CC)(C)C)=CC=1C(CC)(C)C)=O.[O-]CC.[Na+]>CN(C=O)C>[OH:23][CH2:24][N:3]1[C:2]([CH3:1])=[N:6][C:5]([CH3:7])=[N:4]1

Participants

8

Reactant 6

HCID 712FormaldehydeHCID 24386Thionyl ChlorideHCID 1390011H-1,2,4-Triazole, 3,5-dimethyl-HCID 2723922Sodium ethoxideHCID 204424111,4-dihydroxy-N-[gamma-(2,4-di-tert-amylphenoxy)propyl]-2-naphthamideHCID 213266981-Chloromethyl-3,5-dimethyl-1,2,4-triazole

Product 1

HCID 213266971-Hydroxymethyl-3,5-dimethyl-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Hydroxymethyl-3,5-dimethyl-1,2,4-triazole which was prepared from 3,5-dimethyl-1,2,4-triazole and formaldehyde was reacted with 1.5 to 5 times on a molar basis of thionyl chloride to prepare 1-chloromethyl-3,5-dimethyl-1,2,4-triazole. This was reacted with an equimolar amount of 1,4-dihydroxy-N-[γ-(2,4-di-tert-amylphenoxy)propyl]-2-naphthamide in DMF in the presence of 1.5 to 3 times on a molar basis of sodium ethoxide to obtain Coupler (36).

Sources & evidence

ORD record
ord-1e4157c148b84269a4fe0c5d445ebf7d
Source dataset
uspto-grants-1979_03
Patent number
US04146396

Reaction notes

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