Toluene → N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-8-quinolinesulfonamide

HRID 1262793Notes

Reaction equation

HRID 1262793 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11]([NH2:14])(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.C[Al](C)C.[CH3:26][O:27][C:28]1[CH:33]=[C:32]([CH3:34])[N:31]=[C:30]([NH:35][C:36](=O)[O:37]C)[N:29]=1>C(Cl)Cl>[CH3:26][O:27][C:28]1[CH:33]=[C:32]([CH3:34])[N:31]=[C:30]([NH:35][C:36]([NH:14][S:11]([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)(=[O:12])=[O:13])=[O:37])[N:29]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 944648-QuinolinesulfonamideHCID 13072161Methyl (4-methoxy-6-methylpyrimidin-2-yl)carbamateHCID 16682925Trimethylaluminum

Product 1

HCID 13072162N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-8-quinolinesulfonamideYield 47.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 8-quinolinesulfonamide (4.2 g) in 100 ml methylene chloride is added a 2 M toluene solution of trimethylaluminum (15 ml). The resulting solution is stirred under N2 for 45 min. Solid methyl (4-methoxy-6-methylpyrimidin-2-yl)carbamate (4.0 g) is added and the mixture is heated at reflux for 60 hrs. The reaction is quenched sequentially with acetic acid (2 ml) 6 N HCl (5 ml) and water (25 ml). The organic solution is retained, dried with MgSO4, filtered, and is concentrated in vacuo to a crude solid. Washing with methyl acetate afforded 3.6 g of a pale yellow powder m.p. 181°-185° C. The infrared spectrum showed characteristic absorption bands at 3100 and 1700 cm-1.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 60 hrs
  3. customThe reaction is quenched sequentially with acetic acid (2 ml) 6 N HCl (5 ml) and water (25 ml)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationis concentrated in vacuo to a crude solid
  7. washWashing with methyl acetate

Sources & evidence

ORD record
ord-20f12fe65a8a45b2b256904e61c463b9
Source dataset
uspto-grants-1984_06
Patent number
US04453970

Reaction notes

Loading…