Methane → HCID 13364715, compound

HRID 1583880Notes

Reaction equation

HRID 1583880 reaction equation
NN1N=[CH:5][CH:4]=[N:3]1.C[Al](C)C.C.[CH3:12][O:13][C:14]1[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([NH:21][C:22]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34](OC)=[O:35])(=[O:27])=[O:26])=[O:23])[N:15]=1.Cl.[S:39]1C=C[N:41]=[CH:40]1>C(Cl)Cl.C1(C)C=CC=CC=1.C(O)(C(F)(F)F)=O>[CH3:12][O:13][C:14]1[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([NH:21][C:22]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([NH:41][C:40]2[S:39][CH:5]=[CH:4][N:3]=2)=[O:35])(=[O:26])=[O:27])=[O:23])[N:15]=1

Participants

10

Reactant 6

HCID 297MethaneHCID 313Hydrochloric AcidHCID 9256ThiazoleHCID 13176578Methyl 2-[(4-methoxy-6-methyl-pyrimidin-2-yl)carbamoylsulfamoyl]benzoateHCID 16682925TrimethylaluminumHCID 226007512H-1,2,3-Triazol-2-amine

Product 1

HCID 13364715HCID 13364715, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2-aminotriazole (2.1 g) in 100 ml of methylene chloride was added 10 ml of a 2M solution in toluene of trimethylaluminum (1.44 g of Al(CH3)3) by syringe. Evolution of methane gas was seen and the solution became homogeneous. To this mixture was added 4.0 g of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide and the homogeneous solution was heated at reflux for 18 hours. The reaction mixture was then heated with aqueous hydrochloric acid and the precipitated product isolated by filtration, 1.42 g, m.p. 185°-187° C. IR: 1690 cm-1 and 1700 cm-1 unresolved double carbonyl, NMR: in TFA 2.7 ppm s, CH3 pyrimidine, 4.2 ppm s, OCH3 on pyrimidine, 6.7 ppm s, proton in 5-position on pyrimidine, 7.8-8.0 ppm and 8.4-8.5 ppm M, aromatic, 7.6, 7.7 ppm D, thiazole.

Workup

  1. temperaturethe homogeneous solution was heated
  2. temperatureat reflux for 18 hours
  3. customthe precipitated product isolated by filtration, 1.42 g, m.p. 185°-187° C

Sources & evidence

ORD record
ord-55ccb0bf8949465fbeb2da71e6558fbb
Source dataset
uspto-grants-1985_11
Patent number
US04555261

Reaction notes

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