Methylamine → HCID 178485215, compound

HRID 1661444Notes

Reaction equation

HRID 1661444 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([C:14]2[C:23]3[CH2:22][CH2:21][CH2:20][C:19]4[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:18]=4[C:17]=3[N:16]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=3[Cl:36])[N:15]=2)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:43][NH2:44]>ClC1C=CC=CC=1.ClCCl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]=[C:12]([C:14]2[C:23]3[CH2:22][CH2:21][CH2:20][C:19]4[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:18]=4[C:17]=3[N:16]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=3[Cl:36])[N:15]=2)[NH:44][CH3:43])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 6329MethylamineHCID 24819Phosphorus pentachlorideHCID 67309468HCID 67309468, compound

Product 1

HCID 178485215HCID 178485215, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
2.5 °C

Procedure

4-Chloro-N-{8-chloro-1-(2,4-dichloro-phenyl)-1,4,5,6-tetrahydro-1,2-diaza-benzo [e] azulene-3-carbonyl}-benzene-sulfonamide (2.0 g, 3.44 mmol) and PCl5 (1.56 g, 6.88 mmol) in chlorobenzene (20 mL) were refluxed at ca. 120° C. over a period of 3.0 h. The solvents were evaporated under reduced pressure to afford yellow gummy solid. The gummy solid was taken in dichloromethane (15 mL) and cooled to 0-5° C. To this cooled solution, 40% aq. monomethyl amine solution (5.0 mL) was added and stirred at ca. 29° C. over a period of 1 h. The reaction mixture was diluted with water (100 mL) and extracted with dichloromethane. The organic layer was separated, dried over anhydrous Na2SO4 and evaporated under reduced pressure to afford yellow oil. The oil was purified through column chromatography to afford 4-Chloro-N-{[8-chloro-1-(2,4-dichloro-phenyl)-1,4,5,6-tetrahydro-1,2-diaza-benzo [e] azulene-3-yl]-methylamino-methylene}-benzene sulfonamide (0.175 g, 0.294 mmol) as title compound 1, a white solid.

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. customto afford yellow gummy solid
  3. extractionextracted with dichloromethane
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under reduced pressure
  7. customto afford yellow oil
  8. customThe oil was purified through column chromatography

Sources & evidence

ORD record
ord-8c675927865d425c950fb062c20f9e40
Source dataset
uspto-grants-2011_10
Patent number
US08030345B2

Reaction notes

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