Hydrochloric Acid → HCID 20195202, compound

HRID 653207Notes

Reaction equation

HRID 653207 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:14](=[O:17])(=[O:16])[NH2:15])[C:5]2[O:10][S:9](=[O:12])(=[O:11])[CH:8]=[CH:7][C:6]=2[CH:13]=1.[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([N:28](C2C=CC=CC=2)[C:29](=O)[O-:30])[N:21]=1.N12CCCN=C1CCCCC2.Cl>C(#N)C.O>[Br:1][C:2]1[CH:3]=[C:4]([S:14]([NH:15][C:29]([NH:28][C:22]2[N:21]=[C:20]([O:19][CH3:18])[CH:25]=[C:24]([O:26][CH3:27])[N:23]=2)=[O:30])(=[O:17])=[O:16])[C:5]2[O:10][S:9](=[O:12])(=[O:11])[CH:8]=[CH:7][C:6]=2[CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 20195198HCID 20195198, compoundHCID 22104197HCID 22104197, compound

Product 1

HCID 20195202HCID 20195202, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

0.3 g of 6-bromo-8-sulfamoyl-2,2-dioxo-1,2-benzoxathiine are dissolved in 10 ml of acetonitrile. To this solution are added 0.25 g of N-(4,6-dimethoxypyrimidin-2-yl)phenylcarbamate and 0.15 g of 1,8-diazabicyclo[5.4.0]undec-7-ene and the mixture is stirred for 2 hours at 20°-25° C. The mixture is then acidified with 5% hydrochloric acid and diluted with water. The precipitated oil is extracted with ethyl acetate and the combined organic phases are washed with water, dried and concentrated. The oily residue is crystallised from ether, affording 0.3 g of N-(6-bromo-2,2-dioxo-1,2-benzoxathiin-8-ylsulfonyl)-N'-(4,6-dimethoxypyrimidin-2-yl)urea of m.p. 204°-209° C. (decompos.).

Workup

  1. extractionThe precipitated oil is extracted with ethyl acetate
  2. washthe combined organic phases are washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe oily residue is crystallised from ether

Sources & evidence

ORD record
ord-69aad464434442179393841216b535ef
Source dataset
uspto-grants-1987_06
Patent number
US04675417

Reaction notes

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