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

HRID 638367Notes

Reaction equation

HRID 638367 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:15]([NH2:18])(=[O:17])=[O:16])[C:5]2[O:10][S:9](=[O:12])(=[O:11])[C:8]([CH3:13])=[CH:7][C:6]=2[CH:14]=1.N12CCCN=C1CCCCC2.[CH3:30][O:31][C:32]1[N:37]=[C:36]([CH3:38])[N:35]=[C:34]([N:39](C2C=CC=CC=2)[C:40](=O)[O-:41])[N:33]=1>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([S:15]([NH:18][C:40]([NH:39][C:34]2[N:33]=[C:32]([O:31][CH3:30])[N:37]=[C:36]([CH3:38])[N:35]=2)=[O:41])(=[O:16])=[O:17])[C:5]2[O:10][S:9](=[O:11])(=[O:12])[C:8]([CH3:13])=[CH:7][C:6]=2[CH:14]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 135920736-Bromo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamideHCID 199952694-Methoxy-6-methyl-1,3,5-triazin-2-ylphenylcarbamate

Product 1

HCID 13592077N-(6-bromo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaYield 93.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A reaction mixture of 3.54 g of 6-bromo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide, 1.61 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene, 2.73 g of N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)phenylcarbamate and 35 ml of absolute dioxan is stirred for 11/2 hours at room temperature. The solvent is evaporated and the oily residue is triturated with 10 ml of 1N hydrochloric acid and 5 ml of water. The precipitate is isolated by filtration, washed with ether and dried, affording 4.84 g of N-(6-bromo-2,2-dioxo-3-methyl-1,2-benzoxathiin-8ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea of m.p. 196°-198° C.

Workup

  1. customThe solvent is evaporated
  2. customthe oily residue is triturated with 10 ml of 1N hydrochloric acid and 5 ml of water
  3. customThe precipitate is isolated by filtration
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-56b392490558405baac305a02e0b3630
Source dataset
uspto-grants-1985_12
Patent number
US04560771

Reaction notes

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