Triethylamine → HCID 178512367, compound

HRID 1033072Notes

Reaction equation

HRID 1033072 reaction equation
I.[NH2:2][C:3](=[N:5][C:6]1[S:7][CH:8]=[C:9]([C:11]2[O:12][C:13]([CH2:16][N:17]=[C:18]([NH2:21])SC)=[CH:14][CH:15]=2)[N:10]=1)[NH2:4].[N:22]#[C:23][NH2:24].C(N(CC)CC)C>CN(C)C=O>[NH2:2][C:3](=[N:5][C:6]1[S:7][CH:8]=[C:9]([C:11]2[O:12][C:13]([CH2:16][NH:17][C:18]([NH2:21])=[N:24][C:23]#[N:22])=[CH:14][CH:15]=2)[N:10]=1)[NH2:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9864CyanamideHCID 86747810HCID 86747810, compound

Product 1

HCID 178512367HCID 178512367, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(diaminomethyleneamino)-4-[5-(2-methyl-3-isothioureido)methylfuran-2-yl]thiazole hydriodide (1.0 g), cyanamide (120 mg) and triethylamine (1.2 g) in N,N-dimethylformamide (20 ml) was heated at 100° C. for 3 hours. The solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column eluting with a mixture of chloroform and methanol (20:1, V/V). Recrystallization from 20% methanol afforded 2-(diaminomethyleneamino)-4-[5-(2-cyanoguanidino)methylfuran-2-yl]thiazole (170 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was chromatographed on a silica gel column
  3. washeluting with a mixture of chloroform and methanol (20:1, V/V)
  4. customRecrystallization from 20% methanol

Sources & evidence

ORD record
ord-94a1b75104354451b280e17ec207b8d3
Source dataset
uspto-grants-1994_05
Patent number
US05308857

Reaction notes

Loading…