Acetic Acid → N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodithiole-4-sulfonamide

HRID 542685Notes

Reaction equation

HRID 542685 reaction equation
[CH3:1][C:2]1([CH3:15])[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([S:11]([NH2:14])(=[O:13])=[O:12])[C:4]=2[S:3]1.C[Al](C)C.[CH3:20][O:21][C:22]1[N:27]=[C:26]([CH3:28])[N:25]=[C:24]([NH:29][C:30](=O)[O:31]C)[N:23]=1.C(O)(=O)C>C(Cl)Cl.Cl>[CH3:20][O:21][C:22]1[N:27]=[C:26]([CH3:28])[N:25]=[C:24]([NH:29][C:30]([NH:14][S:11]([C:10]2[C:4]3[S:3][C:2]([CH3:15])([CH3:1])[S:6][C:5]=3[CH:7]=[CH:8][CH:9]=2)(=[O:13])=[O:12])=[O:31])[N:23]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 138269262,2-Dimethyl-1,3-Benzodithiole-4-SulfonamideHCID 14404501Methyl (4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamateHCID 16682925Trimethylaluminum

Product 1

HCID 20137759N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodithiole-4-sulfonamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.6 g 2,2-dimethyl-1,3-benzodithiole-4-sulfonamide prepared in Example 7, in 60 ml methylene chloride at room temperature under nitrogen is added 5.5 ml trimethylaluminum (2M in toluene). After stirring 15 minutes at room temperature, 2.0 g of methyl [4-methoxy-6-methyl-1,3,5-triazin-2-yl]carbamate, prepared according to the procedure of Example 5, was added and the reaction mixture was heated at reflux for 72 hours. The reaction mixture was cooled to room temperature and 75 ml ice, 3 ml glacial acetic acid, and 10 drops of 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 an appropriate solvent gave a solid.

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 72 hours
  4. temperatureThe reaction mixture was cooled to room 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 an appropriate solvent
  10. customgave a solid

Sources & evidence

ORD record
ord-ab2d1b475347420790ee23b1371028f3
Source dataset
uspto-grants-1987_04
Patent number
US04659368

Reaction notes

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