Triethylamine → 2-(Diaminomethyleneamino)-4-[2-(furfurylthio)acetylaminomethylthiazol-4-yl]thiazole

HRID 1491864Notes

Reaction equation

HRID 1491864 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:25][CH2:26][C:27](O)=[O:28])[C:20]1[O:24][CH:23]=[CH:22][CH:21]=1.Cl.CN(C)CCCN=C=NCC.C(N(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:27](=[O:28])[CH2:26][S:25][CH2:19][C:20]3[O:24][CH:23]=[CH:22][CH:21]=3)[S:6][CH:7]=2)[N:11]=1)[NH2:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3021476(Furfurylthio)acetic acidHCID 189538344-(2-Aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole dihydrochloride

Product 1

HCID 189538562-(Diaminomethyleneamino)-4-[2-(furfurylthio)acetylaminomethylthiazol-4-yl]thiazoleYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-(2-aminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole dihydrochloride (1.6 g), (furfurylthio)acetic acid (0.98 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.2 g) and triethylamine (1.0 g) in N,N-dimethylformamide (20 ml) was stirred with cooling on an ice-water bath for 2.5 hours. The solvent was removed under the reduced pressure. The residue was washed with water and then chromatographed on a silica gel column eluting with a mixture of chloroform and methanol (10:1). The appropriate fractions was collected and the solvent was removed under the reduced pressure. The residue was suspended in water (20 ml) and the mixture was alkalized to pH 11 with a saturated aqueous potassium carbonate solution. The resulting precipitate was collected by filtration. Recrystallization from a mixture of methanol and water afforded 2-(diaminomethyleneamino)-4-[2-(furfurylthio)acetylaminomethylthiazol-4-yl]thiazole (0.22 g).

Workup

  1. temperaturewith cooling on an ice-water bath for 2.5 hours
  2. customThe solvent was removed under the reduced pressure
  3. washThe residue was washed with water
  4. customchromatographed on a silica gel column
  5. washeluting with a mixture of chloroform and methanol (10:1)
  6. customThe appropriate fractions was collected
  7. customthe solvent was removed under the reduced pressure
  8. filtrationThe resulting precipitate was collected by filtration
  9. customRecrystallization
  10. additionfrom a mixture of methanol and water

Sources & evidence

ORD record
ord-c8316d1772ee4b1c8fb40a3a7bf27bec
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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