Hydrochloric Acid → HCID 15704156, compound

HRID 1033057Notes

Reaction equation

HRID 1033057 reaction equation
[C:1]([CH2:3][C:4]1[O:8][C:7]([C:9]2[N:10]=[C:11]([N:14]=[C:15]([NH2:17])[NH2:16])[S:12][CH:13]=2)=[CH:6][CH:5]=1)#[N:2].Cl.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C.O>[NH2:2][CH2:1][CH2:3][C:4]1[O:8][C:7]([C:9]2[N:10]=[C:11]([N:14]=[C:15]([NH2:17])[NH2:16])[S:12][CH:13]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10399717HCID 10399717, compound

Product 1

HCID 15704156HCID 15704156, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To this mixture was dropwise added a mixture of 4-(5-cyanomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (16.0 g) in tetrahydrofuran (30 ml) for 30 minutes under ice-cooling and the mixture was stirred for an hour at ambient temperature. The reaction mixture was added to a mixture of ethyl acetate and water and the mixture was adjusted to pH 1 with 6N-hydrochloric acid. The separated aqueous layer was adjusted to pH 10 with 10% aqueous sodium hydroxide and the mixture was extraced with a mixture of tetrahydrofuran and ethyl acetate. The extract layer was washed with brine and dired over magnesium sulfate. The solvent was concentrated to give 4-[5-(2-aminoethyl)furan-2-yl]-2-(diaminomethyleneamino)thiazole (4.71 g).

Workup

  1. additionTo this mixture was dropwise added
  2. temperaturecooling
  3. washThe extract layer was washed with brine
  4. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-15b783b6103e4833bbd9b5277f5560a8
Source dataset
uspto-grants-1994_05
Patent number
US05308857

Reaction notes

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