N-[2-(3,3,3-trifluoro-1propen-1yl)phenylsulfonyl]-N'-(4-methoxy-6methyl-1,3,5-triazin-2-yl)urea → Prosulfuron

HRID 1165307Notes

Reaction equation

HRID 1165307 reaction equation
[F:1][C:2]([F:28])([F:27])[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14][C:15]([NH:17][C:18]1[N:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20]([CH3:26])[N:19]=1)=[O:16])(=[O:13])=[O:12].[H][H]>C(OCC)(=O)C.[Pd]>[F:27][C:2]([F:1])([F:28])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14][C:15]([NH:17][C:18]1[N:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20]([CH3:26])[N:19]=1)=[O:16])(=[O:12])=[O:13]

Participants

5

Reactant 2

HCID 53872735N-[2-(3,3,3-trifluoro-1propen-1yl)phenylsulfonyl]-N'-(4-methoxy-6methyl-1,3,5-triazin-2-yl)ureaHCID 178418361HCID 178418361, compound

Product 1

HCID 91751Prosulfuron

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.9 g of N-[2-(3,3,3-trifluoro-1-propenyl)-phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2yl)-urea are dissolved in 50 ml of ethyl acetate; there are then added 1.5 g of a 5% palladium/charcoal catalyst, and the mixture is shaken for 16 hours at 20°-25° C. in a hydrogen atmosphere. The catalyst is filtered off, and the residue is completely concentrated by evaporation and subsequently crystallised from an acetone-ether mixture to thus obtain 2.2 g of N-[2-(3,3,3-trifluoropropyl)-phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-urea, m.p. 157°-158° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe residue is completely concentrated by evaporation
  3. customsubsequently crystallised from an acetone-ether mixture to thus obtain 2.2 g of N-[2-(3,3,3-trifluoropropyl)-phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-urea, m.p. 157°-158° C.

Sources & evidence

ORD record
ord-8435f04ca8a1415dbf33375c50deb675
Source dataset
uspto-grants-1990_03
Patent number
US04908467

Reaction notes

Loading…