Methylamine → HCID 178457493, compound

HRID 1822117Notes

Reaction equation

HRID 1822117 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][N:10]([C:19](=S)[NH:20][S:21]([N:24]([CH2:28][CH3:29])[CH2:25][CH2:26][CH3:27])(=[O:23])=[O:22])[N:9]=2)=[CH:4][CH:3]=1.[CH3:31][NH2:32]>C(#N)C.Cl[Hg]Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][N:10]([C:19]([NH:32][CH3:31])=[N:20][S:21]([N:24]([CH2:28][CH3:29])[CH2:25][CH2:26][CH3:27])(=[O:23])=[O:22])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 113747113-(4-chlorophenyl)-N-(((ethyl)propyl-amino)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-thiocarboxamide

Product 1

HCID 178457493HCID 178457493, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6342AcetonitrileSolvent2×

Procedure

Part B: To a stirred suspension of 3-(4-chlorophenyl)-N-(((ethyl)propyl-amino)sulfonyl)-4-phenyl-4,5-dihydro-1H-pyrazole-1-thiocarboxamide (2.32 gram, 5 mmol) in acetonitrile (20 mL) is added cold methylamine (4 mL). To the resulting solution is added a solution of HgCl2 (1.5 gram) in acetonitrile (10 mL). The resulting black suspension is stirred for four hours. The precipitate is removed by filtration. The filtrate is concentrated in vacuo, dissolved in dichloromethane and successively washed with aqueous 0.5 N NaOH solution and water, dried over Na2SO4, filtered and concentrated in vacuo. The resulting oil is crystallized from diethyl ether to give 3-(4-chlorophenyl)-N′-(((ethyl)propylamino)sulfonyl)-N-methyl-4-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamidine (1.78 gram, 77% yield). Melting point (MP):129-131° C.

Workup

  1. customThe precipitate is removed by filtration
  2. concentrationThe filtrate is concentrated in vacuo
  3. dissolutiondissolved in dichloromethane
  4. washsuccessively washed with aqueous 0.5 N NaOH solution and water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting oil is crystallized from diethyl ether

Sources & evidence

ORD record
ord-af0f90224e1742e4b421692412a4ba3d
Source dataset
uspto-grants-2009_10
Patent number
US07608718B2

Reaction notes

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