Formaldehyde → 2-Tetrazoline-5-thione, 1-(hydroxymethyl)-4-phenyl-

HRID 614703Notes

Reaction equation

HRID 614703 reaction equation
[C:1]1([N:7]2[C:11]([SH:12])=[N:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.S(Cl)(Cl)=O.C1(N2C(=S)N(CCl)N=N2)C=CC=CC=1.[OH:33][C:34]1(C2C=CC3C(=CC=CC=3)C=2C(NOC(CCCCCCCCCCCC)C)=O)C=CC(O)=CC1.[O-]CC.[Na+]>C1C=CC=CC=1.CN(C=O)C>[C:1]1([N:7]2[C:11](=[S:12])[N:10]([CH2:34][OH:33])[N:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

9

Reactant 6

HCID 712FormaldehydeHCID 24386Thionyl ChlorideHCID 2723922Sodium ethoxideHCID 15291093HCID 15291093, compoundHCID 86736426HCID 86736426, compoundHCID 1785279861-phenyltetrazole-5-thiol

Product 1

HCID 2085992-Tetrazoline-5-thione, 1-(hydroxymethyl)-4-phenyl-

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

1-Phenyl-4-hydroxymethyltetrazolin-5-thione which was prepared from 1-phenyl-5-mercaptotetrazole and an excess amount of formaldehyde was reacted with 2 to 5 times on a molar basis of thionyl chloride in benzene at 50° C. for 3 hours to prepare 1-phenyl-4-chloromethyltetrazolin-5-thione. This was reacted with an equimolar amount of 1,4-dihydroxy-N-(2-tetradecyloxy)-phenylnaphthamide in DMF in the presence of 1.5 to 3 times on a molar basis of sodium ethoxide to obtain Coupler (42).

Sources & evidence

ORD record
ord-93c2ed129dcb47a3b98202638c6070c6
Source dataset
uspto-grants-1979_03
Patent number
US04146396

Reaction notes

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