Hydrochloric Acid → N-[2-(3,3,3-trifluoro-1propen-1yl)phenylsulfonyl]-N'-(4-methoxy-6methyl-1,3,5-triazin-2-yl)urea
Reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([N:10](C2C=CC=CC=2)[C:11](=[O:13])[O-])[N:4]=1.[F:20][C:21]([F:35])([F:34])[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30]([NH2:33])(=[O:32])=[O:31].Cl>O1CCOCC1.O>[F:35][C:21]([F:20])([F:34])[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30]([NH:33][C:11]([NH:10][C:5]1[N:4]=[C:3]([O:2][CH3:1])[N:8]=[C:7]([CH3:9])[N:6]=1)=[O:13])(=[O:32])=[O:31]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
5.2 g of N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-phenylcarbamate are added to a solution of 5 g of 2-(3,3,3-trifluoro-1-propen-1-yl)-phenylsulfonamide and 3.3 g of 1,5-diazabicyclo[5,4,0]undec-5-one in 80 ml of dioxan, and the mixture is stirred for 3 hours at 20°-25° C. The clear reaction solution is then taken up in 300 ml of water and the aqueous solution is acidified with 2N hydrochloric acid to pH 4-5. The resinous precipitate is extracted from the aqueous phase with ethyl acetate and the organic extract is dried and concentrated. The oily residue is crystallised from a 1:10 mixture of acetone/ether, affording 7.2 g of the title compound with a melting point of 159°-160° C.
Workup
- extractionThe resinous precipitate is extracted from the aqueous phase with ethyl acetate
- extractionthe organic extract
- customis dried
- concentrationconcentrated
- customThe oily residue is crystallised from a 1:10 mixture of acetone/ether
Sources & evidence
- ORD record
- ord-82f3c59e852841b9b35ae9cadb0d4596
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05041603
Reaction notes
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