Methane → HCID 178494213, compound

HRID 2412307Notes

Reaction equation

HRID 2412307 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([NH:10][C:11]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23](OC)=[O:24])(=[O:16])=[O:15])=[O:12])[N:4]=1.C[Al](C)C.C.[NH2:32][C:33]1[N:37]=[CH:36][NH:35][N:34]=1.Cl>C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([NH:10][C:11]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([NH:32][C:33]2[N:37]=[CH:36][NH:35][N:34]=2)=[O:24])(=[O:15])=[O:16])=[O:12])[N:4]=1

Participants

8

Reactant 5

HCID 297MethaneHCID 313Hydrochloric AcidHCID 52999Metsulfuron-methylHCID 16682925TrimethylaluminumHCID 178418311HCID 178418311, compound

Product 1

HCID 178494213HCID 178494213, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a slurry of 4.0 g of N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide in 100 ml of methylene chloride was added by syringe 10 ml of a 2M solution of trimethylaluminum in toluene (1.44 g of Al(CH3)3). Evolution of methane gas was seen. 3-Amino-1,2,4-triazole (1.7 g) was then added and the mixture was heated at reflux for 18 hours. The reaction mixture was then treated with aqueous hydrochloric acid and the precipitated product was purified by trituration in methylene chloride, 0.63 g, m.p. 176°-179° C. NMR in TFA 2.9 ppm s, CH3 on triazine, 4.4 ppm s, OCH3 on triazine, 7.8-8.0 ppm and 8.2-8.5 ppm M, aromatic.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 18 hours
  3. customthe precipitated product was purified by trituration in methylene chloride

Sources & evidence

ORD record
ord-c79b100db68d498eaa90970b43cf79e6
Source dataset
uspto-grants-1985_01
Patent number
US04491467

Reaction notes

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