2-Furancarbonyl chloride → HCID 10426814, compound

HRID 1033054Notes

Reaction equation

HRID 1033054 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[NH2:9][CH2:10][C:11]1[O:15][C:14]([C:16]2[N:17]=[C:18]([N:21]=[C:22]([NH2:24])[NH2:23])[S:19][CH:20]=2)=[CH:13][CH:12]=1>CN(C)C=O>[NH2:23][C:22](=[N:21][C:18]1[S:19][CH:20]=[C:16]([C:14]2[O:15][C:11]([CH2:10][NH:9][C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[O:7])=[CH:12][CH:13]=2)[N:17]=1)[NH2:24]

Participants

4

Reactant 2

HCID 682422-Furancarbonyl chlorideHCID 103992684-(5-Aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole

Product 1

HCID 10426814HCID 10426814, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Furoyl chloride (0.48 g) was added slowly to a solution of 4-(5-aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (0.80 g) in N,N-dimethylformamide (20 ml) with cooling on an ice bath and the mixture was stirred for an hour with cooling on an ice bath. The solvent was removed under reduced pressure and the residue was chromatographed on a silica gel column eluting with a mixture of chloroform and methanol (30:1, (V/V). Recrystallization from methanol afforded 2-(diaminomethyleneamino)-4-[5-(2-furoyl)aminomethylfuran-2-yl]thiazole (0.20 g).

Workup

  1. temperaturewith cooling on an ice bath
  2. temperaturewith cooling on an ice bath
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was chromatographed on a silica gel column
  5. washeluting with a mixture of chloroform and methanol (30:1, (V/V)
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-035ae5b7005f489bbfcdfeac4840cd88
Source dataset
uspto-grants-1994_05
Patent number
US05308857

Reaction notes

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