Dimethyl N-cyanodithioiminocarbonate → HCID 178503902, compound

HRID 2379834Notes

Reaction equation

HRID 2379834 reaction equation
[NH2:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]2[N:10]=[C:11]([N:14]=[C:15]([NH2:17])[NH2:16])[S:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=1.[CH3:18][S:19][C:20](SC)=[N:21][C:22]#[N:23]>C(O)C>[NH2:16][C:15](=[N:14][C:11]1[S:12][CH:13]=[C:9]([C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][NH:1][C:20](=[N:21][C:22]#[N:23])[S:19][CH3:18])[N:8]=2)[N:10]=1)[NH2:17]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 103997684-(6-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole

Product 1

HCID 178503902HCID 178503902, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (0.50 g) and dimethyl N-cyanodithioiminocarbonate [(CH3S)2C=N-CN] (0.29 g) in ethanol (10 ml) was refluxed for one hour to give 2-(diaminomethyleneamino)-4-[6-(3-cyano-2-methylisothioureido)methylpyridin-2-yl]thiazole of a crude product. After being concentrated to dry the above product, 40 weight % methanolic methylamine (1.6 ml) and N,N-dimethylformamide (10 ml) was added and the mixture was stirred at 60° C. for 5 hours. The solvent was evaporated in vacuo and the residue was mixed with water. The resulting precipitate was collected by filtration and recrystallized from aqueous N,N-dimethylformamide to give 4-[6-(2-cyano-3-methylguanidino)methylpyridin-2-yl]-2-(diaminomethyleneamino)thiazole (0.42 g).

Workup

  1. temperaturewas refluxed for one hour

Sources & evidence

ORD record
ord-b432c1196c634a4183b8dadd5cb8ec5f
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

Loading…