Triethylamine → HCID 178477733, compound

HRID 1491866Notes

Reaction equation

HRID 1491866 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.[CH2:19]([S:21](C(=N)OCC)(=[O:23])=[O:22])[CH3:20].[CH2:29]([N:31](CC)CC)C>CO>[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][CH:29]=[N:31][S:21]([CH2:19][CH3:20])(=[O:22])=[O:23])[S:6][CH:7]=2)[N:11]=1)[NH2:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 189538344-(2-Aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole dihydrochlorideHCID 18953866Ethyl ethanesulfonylformimidate

Product 1

HCID 178477733HCID 178477733, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 4-(2-aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole dihydrochloride (1.3 g), ethyl ethanesulfonylformimidate (0.8 g) and triethylamine (1.0 g) in methanol (20 ml) was stirred at room temperature for 8 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 (10:1). Recrystallization from a mixture of N,N-dimethylformamide and water afforded 2-(diaminomethyleneamino)-4-(2-ethanesulfonyliminomethylaminomethylthiazol-4-yl)thiazole (0.53 g).

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 (10:1)
  4. customRecrystallization
  5. additionfrom a mixture of N,N-dimethylformamide and water

Sources & evidence

ORD record
ord-7739386f68824b17baeda256c80744ff
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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