2-Ethyl-4-amino-6-methoxy-s-triazine → HCID 13729495, compound

HRID 1632634Notes

Reaction equation

HRID 1632634 reaction equation
[F:1][CH:2]([F:23])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13](C1C=CC=CC=1)[C:14](=[O:16])[O-])(=[O:12])=[O:11].[NH2:24][C:25]1[N:30]=[C:29]([CH2:31][CH3:32])[N:28]=[C:27]([O:33][CH3:34])[N:26]=1>O1CCOCC1.C(OCC)(=O)C>[F:23][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]([NH:24][C:25]1[N:30]=[C:29]([CH2:31][CH3:32])[N:28]=[C:27]([O:33][CH3:34])[N:26]=1)=[O:16])(=[O:11])=[O:12]

Participants

5

Reactant 2

HCID 697012-Ethyl-4-amino-6-methoxy-s-triazineHCID 86739686HCID 86739686, compound

Product 1

HCID 13729495HCID 13729495, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 5.4 g of N-(2-difluoromethoxyphenylsulfonyl)phenylcarbamate and 2.42 g of 2-amino-4-ethyl-6-methoxy-1,3,5-triazine in 60 ml of dioxane is refluxed for 5 hours and then poured into 600 ml of ice-water. The precipitate is taken up in ethyl acetate. The ethyl acetate phase is washed with water, dried and concentrated. The residual oil is dissolved in ethyl acetate and washed 5 times with saturated sodium bicarbonate solution. The combined aqueous phases are acidified with dilute hydrochloric acid and extracted with ethyl acetate. The ethyl acetate phase is dried and evaporated to dryness. Recrystallisation from methanol yields 5.1 g of N-(2-difluoromethoxyphenylsulfonyl)-N'-(4-ethyl-6-methoxy-1,3,5-triazin-2-yl)urea with a melting point of 114°-116° C.

Workup

  1. washThe ethyl acetate phase is washed with water
  2. customdried
  3. concentrationconcentrated
  4. dissolutionThe residual oil is dissolved in ethyl acetate
  5. washwashed 5 times with saturated sodium bicarbonate solution
  6. extractionextracted with ethyl acetate
  7. dry with materialThe ethyl acetate phase is dried
  8. customevaporated to dryness
  9. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-2d595dc20e794fc49361d7f8ec71b963
Source dataset
uspto-grants-1984_10
Patent number
US04476321

Reaction notes

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