Toluene → HCID 15589116, compound

HRID 1164408Notes

Reaction equation

HRID 1164408 reaction equation
[Cl:1][C:2]1[C:11]([S:12]([NH2:15])(=[O:14])=[O:13])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.C[Al](C)C.C[O:28][C:29](=O)[NH:30][C:31]1[N:36]=[C:35]([O:37][CH3:38])[N:34]=[C:33]([O:39][CH3:40])[N:32]=1>C(Cl)Cl>[Cl:1][C:2]1[C:11]([S:12]([NH:15][C:29]([NH:30][C:31]2[N:32]=[C:33]([O:39][CH3:40])[N:34]=[C:35]([O:37][CH3:38])[N:36]=2)=[O:28])(=[O:14])=[O:13])=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 12803256Methyl (4,6-dimethoxy-1,3,5-triazin-2-yl)carbamateHCID 16682925TrimethylaluminumHCID 20455845HCID 20455845, compound

Product 1

HCID 15589116HCID 15589116, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 7-chloro-8-quinolinesulfonamide (1.5 g) in 75 ml methylene chloride is added a 2 M toluene solution of trimethyl aluminum (4.7 ml). The resulting solution is stirred under N2 for 45 min. Solid methyl(4,6-dimethoxy-1,3,5-triazin-2-yl)carbamate (1.1 g) is added and the mixture is heated at reflux for 60 h. The reaction is quenched sequentially with acetic acid (1 ml), 6 N HCl (2.5 ml) and water (13 ml). The organic solution is retained, dried with MgSO4, and is concentrated to an oil-solid mixture. Filtration afforded 0.6 g yellow solid m.p. 169°-191° C. (dec). The infrared spectrum showed characteristic absorption bands at 3300 and 1700 cm-1.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 60 h
  3. customThe reaction is quenched sequentially with acetic acid (1 ml), 6 N HCl (2.5 ml) and water (13 ml)
  4. dry with materialdried with MgSO4
  5. concentrationis concentrated to an oil-solid mixture
  6. filtrationFiltration

Sources & evidence

ORD record
ord-d9de013824134392b06619ea69f893e5
Source dataset
uspto-grants-1983_01
Patent number
US04369320

Reaction notes

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