Methylamine → HCID 178485037, compound

HRID 1033050Notes

Reaction equation

HRID 1033050 reaction equation
[NH2:1][CH2:2][C:3]1[O:7][C:6]([C:8]2[N:9]=[C:10]([N:13]=[C:14]([NH2:16])[NH2:15])[S:11][CH:12]=2)=[CH:5][CH:4]=1.CS[C:19](SC)=[N:20][C:21]#[N:22].[CH3:25][NH2:26]>CN(C)C=O>[NH2:15][C:14](=[N:13][C:10]1[S:11][CH:12]=[C:8]([C:6]2[O:7][C:3]([CH2:2][NH:1][C:19]([NH:26][CH3:25])=[N:20][C:21]#[N:22])=[CH:4][CH:5]=2)[N:9]=1)[NH2:16]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 103992684-(5-Aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole

Product 1

HCID 178485037HCID 178485037, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(5-aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (7.00 g) and dimethyl N-cyanodithioiminocarbonate (4.31 g) in N,N-dimethylformamide (70 ml) was stirred at 70° C. for two hours. 40% Aqueous methylamine by weight (14 ml) was added to the warmed solution and the mixture was stirred for an additional one hour at the same temperature. After the solvent was evaporated in vacuo, the residue was chromatographed on alumina, eluting with a mixture of chloroform and methanol (9:1, V/V), followed by recrystallization from a mixture of methanol, tetrahydrofuran and diisopropyl ether to afford 2-(diaminomethyleneamino)-4-[5-(2-cyano-3-methylguanidino)methylfuran-2-yl]thiazole (4.05 g).

Workup

  1. customAfter the solvent was evaporated in vacuo
  2. customthe residue was chromatographed on alumina
  3. washeluting with a mixture of chloroform and methanol (9:1, V/V)
  4. customfollowed by recrystallization from a mixture of methanol, tetrahydrofuran and diisopropyl ether

Sources & evidence

ORD record
ord-d16879bb2bd54dc0a052fd66b7be1ec5
Source dataset
uspto-grants-1994_05
Patent number
US05308857

Reaction notes

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