2-Amino-4-methoxy-6-methyl-1,3,5-triazine → N-(3-Chloropyridazine-6-sulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea

HRID 247469

Reaction equation

HRID 247469 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([S:8]([N:11](C2C=CC=CC=2)[C:12](=[O:14])[O-])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[NH2:21][C:22]1[N:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([CH3:30])[N:23]=1>O1CCOCC1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([S:8]([NH:11][C:12]([NH:21][C:22]2[N:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([CH3:30])[N:23]=2)=[O:14])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 154662-Amino-4-methoxy-6-methyl-1,3,5-triazineHCID 86741701N-(3-chloropyridazine-6-sulfonyl)phenylcarbamate

Product 1

HCID 21275743N-(3-Chloropyridazine-6-sulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaYield 43.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 14.2 g of N-(3-chloropyridazine-6-sulfonyl)phenylcarbamate and 6.3 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine are refluxed for 1 hour in 120 ml of absolute dioxan. When the reaction is complete, the mixture is concentrated in vacuo and the residue is taken up in a saturated aqueous solution of sodium bicarbonate and the insoluble constituents are extracted with methylene chloride. The aqueous phase is acidified with dilute hydrochloric acid and extracted with methylene chloride. The methylene chloride solution is dried over sodium sulfate and concentrated, affording 7 g of the compound of the above formula with a melting point of 135° C.

Workup

  1. concentrationthe mixture is concentrated in vacuo
  2. extractionthe insoluble constituents are extracted with methylene chloride
  3. extractionextracted with methylene chloride
  4. dry with materialThe methylene chloride solution is dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cc3cf87295054356b17909d3b9a248d0
Source dataset
uspto-grants-1987_11
Patent number
US04707551

Linked notes

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