Water → N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,4-benzodioxan-5-sulfonamide

HRID 542688Notes

Reaction equation

HRID 542688 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([S:11]([NH2:14])(=[O:13])=[O:12])[C:5]=2[O:4][CH2:3][CH2:2]1.C[Al](C)C.C[O:20][C:21](=O)[NH:22][C:23]1[N:28]=[C:27]([O:29][CH3:30])[CH:26]=[C:25]([CH3:31])[N:24]=1.O>C(Cl)Cl.Cl.C(O)(=O)C>[CH3:30][O:29][C:27]1[CH:26]=[C:25]([CH3:31])[N:24]=[C:23]([NH:22][C:21]([NH:14][S:11]([C:10]2[C:5]3[O:4][CH2:3][CH2:2][O:1][C:6]=3[CH:7]=[CH:8][CH:9]=2)(=[O:12])=[O:13])=[O:20])[N:28]=1

Participants

8

Reactant 4

HCID 962WaterHCID 13072161Methyl (4-methoxy-6-methylpyrimidin-2-yl)carbamateHCID 134554282,3-Dihydro-1,4-benzodioxine-5-sulfonamideHCID 16682925Trimethylaluminum

Product 1

HCID 13455430N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,4-benzodioxan-5-sulfonamide

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.0 g 1,4-benzodioxan-5-sulfonamide, prepared in Example 15, in 50 ml methylene chloride at ambient temperature under nitrogen was added 2.5 ml trimethylaluminum (2M in toluene). After stirring 15 minutes at ambient temperature, 1.0 g of methyl[4-methoxy-6-methylpyrimidin-2-yl]carbamate, prepared according to the procedure of Example 3, was added and the reaction mixture was heated at reflux for 72 hours. The reaction mixture was cooled to ambient temperature and 75 ml water, 10 ml glacial acetic acid and 10 drops hydrochloric acid were sequentially added. The organic phase was separated, dried, and the solvent removed under reduced pressure to give an oil. Crystallization of the oil from n-butyl chloride/ether gave a solid, m.p. 203°-205° C.

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 72 hours
  4. temperatureThe reaction mixture was cooled to ambient temperature
  5. customThe organic phase was 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. customgave a solid, m.p. 203°-205° C.

Sources & evidence

ORD record
ord-28d558f51c7d45fb9884936b786897c0
Source dataset
uspto-grants-1987_04
Patent number
US04659368

Reaction notes

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