Water → N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,3-benzoxathiole-4-sulfonamide

HRID 1982097Notes

Reaction equation

HRID 1982097 reaction equation
[O:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([S:10]([NH2:13])(=[O:12])=[O:11])=[C:4]2[S:3][CH2:2]1.C[Al](C)C.C[O:19][C:20](=O)[NH:21][C:22]1[N:27]=[C:26]([O:28][CH3:29])[CH:25]=[C:24]([CH3:30])[N:23]=1.O>C(Cl)Cl.Cl.C(O)(=O)C>[CH3:29][O:28][C:26]1[CH:25]=[C:24]([CH3:30])[N:23]=[C:22]([NH:21][C:20]([NH:13][S:10]([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[O:1][CH2:2][S:3][C:4]=23)(=[O:12])=[O:11])=[O:19])[N:27]=1

Participants

8

Reactant 4

HCID 962WaterHCID 13072161Methyl (4-methoxy-6-methylpyrimidin-2-yl)carbamateHCID 16682925TrimethylaluminumHCID 201377521,3-Benzoxathiole-4-sulfonamide

Product 1

HCID 20137750N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,3-benzoxathiole-4-sulfonamide

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.2 g 1,3-benzoxathiole-4-sulfonamide, prepared in Example 13, in 50 ml methylene chloride at ambient temperature under nitrogen is added 5.5 ml trimethylaluminum (2M in toluene). After stirring 15 minutes at ambient temperature, 2.0 g of methyl[4-methoxy-6-methylpyrimidin-2-yl]carbamate, prepared according to the procedure of Example 3, is added and the reaction mixture is heated at reflux for 16 hours. The reaction mixture is cooled to ambient temperature and 75 ml water, 10 ml glacial acetic acid, and 10 drops hydrochloric acid are sequentially added. The organic phase is separated, dried, and the solvent removed under reduced pressure to give an oil. Crystallization of the oil from n-butyl chloride/ether gives a solid.

Workup

  1. additionis added
  2. temperaturethe reaction mixture is heated
  3. temperatureat reflux for 16 hours
  4. temperatureThe reaction mixture is cooled to ambient temperature
  5. customThe organic phase is separated
  6. customdried
  7. customthe solvent removed under reduced pressure
  8. customto give an oil
  9. customCrystallization of the oil from n-butyl chloride/ether
  10. customgives a solid

Sources & evidence

ORD record
ord-652dc0895c1c4e03a66922b3ec3defd7
Source dataset
uspto-grants-1986_06
Patent number
US04595407

Reaction notes

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