Hydrochloric Acid → 3-(1,3-Dioxolan-2-yl)-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophenesulfonamide

HRID 1723308Notes

Reaction equation

HRID 1723308 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[S:11]([NH2:14])(=[O:13])=[O:12].C1([O:21][C:22](=O)[NH:23][C:24]2[N:29]=[C:28]([O:30][CH3:31])[N:27]=[C:26]([CH3:32])[N:25]=2)C=CC=CC=1.N12CCCN=C1CCCCC2.Cl>C(#N)C.O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[S:11]([NH:14][C:22]([NH:23][C:24]1[N:29]=[C:28]([O:30][CH3:31])[N:27]=[C:26]([CH3:32])[N:25]=1)=[O:21])(=[O:13])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11448329Carbamic acid, (4-methoxy-6-methyl-1,3,5-triazin-2-yl)-, phenyl esterHCID 138817523-(1,3-Dioxolan-2-yl)thiophene-2-sulfonamide

Product 1

HCID 138817533-(1,3-Dioxolan-2-yl)-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-thiophenesulfonamideYield 74.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 0.47 g of 3-(1,3-dioxolan-2-yl)thiophene-2-sulfonamide in 20 ml of acetonitrile was added 0.52 g of phenyl(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate and 0.3 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). After stirring at ambient temperatures for two hours the solution was diluted to 50 ml with water and the pH was adjusted to 3 by the addition of hydrochloride acid. The resultant solution was extracted with methylene chloride and the methylene chloride phase was dried over magnesium sulfate, filtered and evaporated. Trituration of the residue with butyl chloride yielded 0.6 g of the product, m.p. 164°-166°. Infrared absorption spectra showed peaks at 1700, 1600 and 1550 cm-1, consistent for the desired structure. ##STR27##

Workup

  1. extractionThe resultant solution was extracted with methylene chloride
  2. dry with materialthe methylene chloride phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-3144a6955d6140e981cd2d1f2fdf0d54
Source dataset
uspto-grants-1989_08
Patent number
US04861366

Reaction notes

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