HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → 2-(Diaminomethyleneamino)-4-[2-(2-cyano-3-methylguanidino)methylthiazol-4-yl]thiazole

HRID 2379858
Notes
Print preview

Reaction equation

HRID 2379858 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10]2[N:11]=[C:12]([N:15]=[C:16]([NH2:18])[NH2:17])[S:13][CH:14]=2)[N:9]=1.[C:19]([N:21]=[C:22](SC)SC)#[N:20].[CH2:27]([N:29](CC)CC)C>CN(C)C=O>[NH2:17][C:16](=[N:15][C:12]1[S:13][CH:14]=[C:10]([C:8]2[N:9]=[C:5]([CH2:4][NH:3][C:19]([NH:21][CH3:22])=[N:20][C:27]#[N:29])[S:6][CH:7]=2)[N:11]=1)[NH2:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 189538344-(2-Aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole dihydrochloride

Product 1

HCID 1784850392-(Diaminomethyleneamino)-4-[2-(2-cyano-3-methylguanidino)methylthiazol-4-yl]thiazoleYield 19.5%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
70 °C

Procedure

A suspension of 4-(2-aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole dihydrochloride (1.0 g), dimethyl N-cyanodithiocarbonimidate (0.45 g) and triethyl amine (0.7 g) in N,N-dimethylformamide (40 ml) was heated at 70° C. for 10 hours. 40% methylamino solution (5 ml) was added to the reaction mixture and the mixture was stirred at room temperature for 14 hours. The solvent was removed under reduced pressure. The residue was suspended in water (30 ml) and the mixture was alkalized to pH 10 with a saturated aqueous potassium carbonate solution. The resulting precipitate was collected by filtration. Recrystallization from a mixture of N,N-dimethylformamide and water afforded 2-(diaminomethyleneamino)-4-[2-(2-cyano-3-methylguanidino)methylthiazol-4-yl]thiazole (0.2 g).

Workup

  1. addition40% methylamino solution (5 ml) was added to the reaction mixture
  2. customThe solvent was removed under reduced pressure
  3. filtrationThe resulting precipitate was collected by filtration
  4. customRecrystallization
  5. additionfrom a mixture of N,N-dimethylformamide and water

Sources & evidence

ORD record
ord-29a58ccdc8314aff82cd1de97e231220
Source dataset
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05364871

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes