1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea

HRID 638368Notes

Reaction equation

HRID 638368 reaction equation
[O:1]=[S:2]1(=[O:17])[C:7]([CH3:8])=[CH:6][C:5]2[CH:9]=[CH:10][CH:11]=[C:12]([S:13]([NH2:16])(=[O:15])=[O:14])[C:4]=2[O:3]1.N12CCCN=C1CCCCC2.[CH3:29][O:30][C:31]1[N:36]=[C:35]([CH3:37])[N:34]=[C:33]([N:38](C2C=CC=CC=2)[C:39](=O)[O-:40])[N:32]=1>O1CCOCC1.C(#N)C>[O:17]=[S:2]1(=[O:1])[C:7]([CH3:8])=[CH:6][C:5]2[CH:9]=[CH:10][CH:11]=[C:12]([S:13]([NH:16][C:39]([NH:38][C:33]3[N:32]=[C:31]([O:30][CH3:29])[N:36]=[C:35]([CH3:37])[N:34]=3)=[O:40])(=[O:14])=[O:15])[C:4]=2[O:3]1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 135920743-Methyl-8-sulfamoyl-2,2-dioxo-1,2-benzoxathiineHCID 199952694-Methoxy-6-methyl-1,3,5-triazin-2-ylphenylcarbamate

Product 1

HCID 13592078N-(2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaYield 97.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3.3 g of 2,2-dioxo-3-methyl-1,2-benzoxathiin-8-yl sulfonamide, 1.90 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene, 3.28 g of N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)phenylcarbamate in a mixture of 25 ml of dioxan and 10 ml of acetonitrile is stirred at 20° C. to 25° C. for 1 hour. The solvents are evaporated and the residue is triturated with a mixture of 7 ml of 2N hydrochloric acid and 10 ml of water and then with 20 ml of ether. The precipitate is isolated by filtration and dried, affording 5.14 g of N-(2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea of m.p. 203°-205° C.

Workup

  1. customThe solvents are evaporated
  2. customthe residue is triturated with a mixture of 7 ml of 2N hydrochloric acid and 10 ml of water
  3. customThe precipitate is isolated by filtration
  4. customdried

Sources & evidence

ORD record
ord-05b22efc5a464e0aae2eda0e77ab04b2
Source dataset
uspto-grants-1985_12
Patent number
US04560771

Reaction notes

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