Diethyl Ether → 2-[2-(4,6-Dimethoxypyrimidin-2-yloxy)-6-fluorophenylsulfamoyl]-N-methylacetamide

HRID 743984Notes

Reaction equation

HRID 743984 reaction equation
[CH3:1][NH2:2].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[N:8]=[C:7]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=2[NH:21][S:22]([CH2:25][C:26]([O:28]C)=O)(=[O:24])=[O:23])[N:6]=1.C(OCC)C.C(O)(C)C>CO>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[N:8]=[C:7]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=2[NH:21][S:22]([CH2:25][C:26]([NH:2][CH3:1])=[O:28])(=[O:24])=[O:23])[N:6]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 3776IsopropanolHCID 6329MethylamineHCID 54135497Methyl [2-(4,6-dimethoxypyrimidin-2-yloxy)-6-fluorophenylsulfamoyl]acetate

Product 1

HCID 541152332-[2-(4,6-Dimethoxypyrimidin-2-yloxy)-6-fluorophenylsulfamoyl]-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methylamine (4.2 g of a 33% solution in industrial methylated spirits) was added to a solution of the product of stage (a) (3 g) in methanol (60 ml) at room temperature. After standing for 23 days, the solution was run down under vacuum at less than 35° C. to give a brown oil. Trituration with a mixture of diethyl ether and isopropanol gave an off-white solid which was dried without heat to give 1.3 g of the desired product, mp 193°-198° C.

Workup

  1. customwas run down under vacuum at less than 35° C.
  2. customto give a brown oil
  3. customgave an off-white solid which
  4. customwas dried
  5. temperaturewithout heat

Sources & evidence

ORD record
ord-cd7f04f5e30941738c179d2ee8e27925
Source dataset
uspto-grants-1996_09
Patent number
US05559081

Reaction notes

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