Triethylamine → HCID 178512616, compound

HRID 1033062Notes

Reaction equation

HRID 1033062 reaction equation
[NH2:1][CH2:2][C:3]1[O:7][C:6]([C:8]2[N:9]=[C:10]([N:13]=[C:14]([NH2:16])[NH2:15])[S:11][CH:12]=2)=[CH:5][CH:4]=1.Cl[C:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[S:20](=[O:28])(=[O:27])[N:19]=1.C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.O1CCCC1.C(OC(=O)C)C>[NH2:15][C:14](=[N:13][C:10]1[S:11][CH:12]=[C:8]([C:6]2[O:7][C:3]([CH2:2][NH:1][C:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[S:20](=[O:27])(=[O:28])[N:19]=3)=[CH:4][CH:5]=2)[N:9]=1)[NH2:16]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 64783Pseudosaccharin chlorideHCID 103992684-(5-Aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole

Product 1

HCID 178512616HCID 178512616, compoundYield 36.1%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

An ice-cooling mixture of 4-(5-aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (0.8 g), 3-chlorobenzoisothiazol-1,1-dioxide (0.8 g) and triethylamine (0.5 ml) in N,N-dimethylformamide (15 ml) was stirred for 3 hours. To a reaction mixture was added a mixture of ethylacetate, tetrahydrofuran and water and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed by concentration and a residue was recrystallized from a mixture of methanol, dioxane and diisopropyl ether to give 2-(diaminomethyleneamino)-4-[5-(1,1-dioxobenzoisothiazol-3-yl)aminomethylfuran-2-yl]thiazole (0.49 g).

Workup

  1. additionTo a reaction mixture was added
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed by concentration
  5. customa residue was recrystallized from a mixture of methanol, dioxane and diisopropyl ether

Sources & evidence

ORD record
ord-9fb441714b154ae897d5f946f0bfa6b6
Source dataset
uspto-grants-1994_05
Patent number
US05308857

Reaction notes

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