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

HRID 653519Notes

Reaction equation

HRID 653519 reaction equation
[O:1]=[S:2]1(=[O:17])[CH:7]([CH3:8])[CH2:6][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[CH:36]=[C:35]([CH3:37])[N:34]=[C:33]([N:38](C2C=CC=CC=2)[C:39](=O)[O-:40])[N:32]=1>O1CCOCC1>[O:17]=[S:2]1(=[O:1])[CH:7]([CH3:8])[CH2:6][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])[CH:36]=[C:35]([CH3:37])[N:34]=3)=[O:40])(=[O:14])=[O:15])[C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 135920753,4-Dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamideHCID 18954641N-(4-methoxy-6-methylpyrimidin-2-yl)phenylcarbamate

Product 1

HCID 13592076N-(3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl)-N'-(4-methoxy-6-methylpyrimidin-2-yl)ureaYield 93.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3.33 g of 3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonamide, 1.84 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene, 3.2 g of N-(4-methoxy-6-methylpyrimidin-2-yl)phenylcarbamate and 35 ml of absolute dioxane is stirred for 45 minutes at a temperature of 20° to 25° C. The solvent is destilled off and the oily residue is triturated with ether and 14 ml of 1N hydrochloric acid. The precipitate is separated, washed with water and dried, affording 4.96 g of N-(3,4-dihydro-2,2-dioxo-3-methyl-1,2-benzoxathiin-8-ylsulfonyl)-N'-(4-methoxy-6-methylpyrimidin-2-yl)urea with a melting point of 215°-218° C.

Workup

  1. customthe oily residue is triturated with ether and 14 ml of 1N hydrochloric acid
  2. customThe precipitate is separated
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-50eff9ab622e474ea06b0c5a71c8aba3
Source dataset
uspto-grants-1987_06
Patent number
US04677212

Reaction notes

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