Methylamine → HCID 178485036, compound

HRID 1734027Notes

Reaction equation

HRID 1734027 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:11]2[N:12]=[C:13]([N:16]=[C:17]([NH2:19])[NH2:18])[S:14][CH:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CS[C:22](SC)=[N:23][C:24]#[N:25].[CH3:28][NH2:29]>CN(C)C=O>[NH2:18][C:17]([NH2:19])=[N:16][C:13]1[S:14][CH:15]=[C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([CH2:2][NH:1][C:22]([NH:29][CH3:28])=[N:23][C:24]#[N:25])[CH:4]=2)[N:12]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 19439685HCID 19439685, compound

Product 1

HCID 178485036HCID 178485036, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(3-aminomethyl-4-methoxyphenyl)-2(diaminomethyleneamino)thiazole (350 mg) and N-[di(methylthio)methylene]cyanamide (190 mg) in N,N-dimethylformamide (20 ml) was heated at 70° C. for 2.5 hours. After cooling, 40% methylamine solution (6 ml) was added to the mixture and the mixture was stirred for 5 hours at room temperature. The solvent was removed under reduced pressure and the residue was chromatographed on a silica gel column eluting with a mixture of chloroform and methanol (10:1). Recrystallization from a mixture of methanol and diisopropyl ether afforded 2-(diamino-methyleneamino)-4-[3-{(3-methyl-2-cyanoguanidino)methyl}-4-methoxyphenyl]thiazole (180 mg).

Workup

  1. temperatureAfter cooling
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was chromatographed on a silica gel column
  4. washeluting with a mixture of chloroform and methanol (10:1)
  5. customRecrystallization
  6. additionfrom a mixture of methanol and diisopropyl ether

Sources & evidence

ORD record
ord-c9cb92bd871641ce802c6a604a295924
Source dataset
uspto-grants-1996_07
Patent number
US05532258

Reaction notes

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