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

HRID 2164205Notes

Reaction equation

HRID 2164205 reaction equation
[CH3:1][C:2]1([CH3:15])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([S:11]([NH2:14])(=[O:13])=[O:12])[C:4]=2[O: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[O:3][C:2]([CH3:15])([CH3:1])[O: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 134554192,2-Dimethyl-1,3-benzodioxole-4-sulfonamideHCID 14404501Methyl (4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamateHCID 16682925Trimethylaluminum

Product 1

HCID 13455421N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamideYield 7.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.0 g 2,2-dimethyl-1,3-benzodioxole-4-sulfonamide, prepared in Example 1, in 50 ml methylene chloride a room temperature under nitrogen was added 2.5 ml trimethylaluminum (2M in toluene). After stirring 15 minutes at room temperature, 0.7 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 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 a mixture of ether, methylene chloride, and hexane gave 0.1 g of white solid, m.p. 160°-168° C. The infrared spectrum showed a carbonyl absorption at 1705 cm-1 indicative of the title compound.

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux 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
  10. additionfrom a mixture of ether, methylene chloride, and hexane

Sources & evidence

ORD record
ord-5183b48558a749ebb91ed173be78fbfc
Source dataset
uspto-grants-1985_03
Patent number
US04502882

Reaction notes

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