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 638366Notes

Reaction equation

HRID 638366 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 dioxan is stirred for 45 minutes at a temperature in the range from 20° to 25° C. The mixture is concentrated and the oily residue is triturated with ether and 14 ml of 1N hydrochloric acid. The crystalline precipitate obtained is isolated, 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 of m.p. 215°-218° C.

Workup

  1. concentrationThe mixture is concentrated
  2. customthe oily residue is triturated with ether and 14 ml of 1N hydrochloric acid
  3. customThe crystalline precipitate obtained
  4. customis isolated
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-b29a3fced5634c88a7d392879072aef3
Source dataset
uspto-grants-1985_12
Patent number
US04560771

Reaction notes

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