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

HRID 2248952Notes

Reaction equation

[F:1][C:2]([F:18])([F:17])[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([N:14]=[C:15]=[O:16])(=[O:13])=[O:12].[NH2:19][C:20]1[N:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([CH3:28])[N:21]=1>O1CCOCC1>[F:18][C:2]([F:1])([F:17])[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:19][C:20]1[N:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([CH3:28])[N:21]=1)=[O:16])(=[O:13])=[O:12]

Participants

Conditions

Temperature: 20 °C

Procedure

5.6 g of 2-(3,3,3-trifluoro-1-propen-1-yl)phenylsulfonyl isocyanate and 2.5 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine are stirred in absolute dioxan for 3 hours at 70°-80° C. After it has been cooled to 20° C., the reaction mixture is filtered and the clear solution so obtained is concentrated to a quarter of its volume. Then 50 ml of ether are added and 5.0 g of N-[2-(3,3,3-trifluoro-1-propen-1-yl)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea crystallise from the solution. Melting point: 154°-155° C.

Workup

filtrationthe reaction mixture is filtered
customthe clear solution so obtained
concentrationis concentrated to a quarter of its volume
additionThen 50 ml of ether are added
custom5.0 g of N-[2-(3,3,3-trifluoro-1-propen-1-yl)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea crystallise from the solution

Sources & evidence

ORD record: ord-46d95f59e123494c8b9abb216eb74957
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05041603

Reaction notes

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