Formic Acid → 2-(Diaminomethyleneamino)-4-(5-formamidomethylfuran-2-yl)thiazole

HRID 1033066Notes

Reaction equation

HRID 1033066 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[NH2:11][CH2:12][C:13]1[O:17][C:16]([C:18]2[N:19]=[C:20]([N:23]=[C:24]([NH2:26])[NH2:25])[S:21][CH:22]=2)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CN(C)C=O.O.C(OCC)(=O)C>[NH2:25][C:24](=[N:23][C:20]1[S:21][CH:22]=[C:18]([C:16]2[O:17][C:13]([CH2:12][NH:11][CH:8]=[O:10])=[CH:14][CH:15]=2)[N:19]=1)[NH2:26]

Participants

9

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 103992684-(5-Aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole

Product 1

HCID 157041622-(Diaminomethyleneamino)-4-(5-formamidomethylfuran-2-yl)thiazole

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of acetic anhydride (2.4 ml) and formic acid (1.0 ml) was stirred for 30 minutes at 50° to 60° C. The above mixture was added to a mixture of 4-(5-aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (1.5 g) in tetrahydrofuran (15 ml) and N,N-dimethylformamide (15 ml) at ambient temperature and the mixture was stirred for 2.5 hours at ambient temperature. To the reaction mixture was added a mixture of ethyl acetate, tetrahydrofuran and water and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was washed with a brine and dried over magnesium sulfate. The solvent was removed by concentratoin in vacuo and the residue was recrystallized from a mixture of methanol, dioxane and tetrahydrofuran to give 2-(diaminomethyleneamino)-4-(5-formamidomethylfuran-2-yl)thiazole (0.80 g).

Workup

  1. stirringthe mixture was stirred for 2.5 hours at ambient temperature
  2. additionTo the reaction mixture was added
  3. washThe separated organic layer was washed with a brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed by concentratoin in vacuo
  6. customthe residue was recrystallized from a mixture of methanol, dioxane and tetrahydrofuran

Sources & evidence

ORD record
ord-2b1ff9aa48e34a8486c1a42eb312176c
Source dataset
uspto-grants-1994_05
Patent number
US05308857

Reaction notes

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