Metribuzin → HCID 21387764, compound

HRID 1833825Notes

Reaction equation

HRID 1833825 reaction equation
[NH2:1][N:2]1[C:7](=[O:8])[C:6]([C:9]([CH3:12])([CH3:11])[CH3:10])=[N:5][N:4]=[C:3]1[S:13][CH3:14].O.[C:16]([OH:20])(=[O:19])[CH:17]=[O:18]>C(OCC)(=O)C>[CH3:14][S:13][C:3]1[N:2]([NH:1][CH:17]([OH:18])[C:16]([OH:20])=[O:19])[C:7](=[O:8])[C:6]([C:9]([CH3:11])([CH3:10])[CH3:12])=[N:5][N:4]=1

Participants

4

Reactant 2

HCID 30479MetribuzinHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 21387764HCID 21387764, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

21.4 g (0.1 mol) of 4-amino-6-tert.-butyl-3-methylthio-1,2,4-triazin-5-one and 10.1 g (0.11 mol) of glyoxylic acid monohydrate were stirred in 250 ml of ethyl acetate for 12 hours at room temperature, whereby a clear solution was produced. The mixture was then left to stand; after about 3 hours, the product began to crystallize out. It was filtered off and the filtrate was concentrated, whereupon further material crystallized out. The combined filter residues were washed with ether and dried. 25.2 g (87.5% of theory) of N-(3-methylthio-6-tert.-butyl-1,2,4-triazin-5-on-4-yl)- α-hydroxy-glycine of melting point 161° C (decomposition) were obtained.

Workup

  1. customwhereby a clear solution was produced
  2. waitThe mixture was then left
  3. customto crystallize out
  4. filtrationIt was filtered off
  5. concentrationthe filtrate was concentrated, whereupon further material
  6. customcrystallized out
  7. filtrationThe combined filter residues
  8. washwere washed with ether
  9. customdried

Sources & evidence

ORD record
ord-84691104462240d49786aeed9a875f36
Source dataset
uspto-grants-1978_01
Patent number
US04067724

Reaction notes

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