Triethylamine → HCID 18956307, compound

HRID 2379826Notes

Reaction equation

HRID 2379826 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].Cl.Cl.Cl.[NH2:10][C:11]1[S:12][CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][NH2:23])[N:17]=2)[N:15]=1.C(N(CC)CC)C>CN(C)C=O.O1CCCC1>[NH2:10][C:11]1[S:12][CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][NH:23][C:2]([O:4][CH2:5][CH3:6])=[O:3])[N:17]=2)[N:15]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 18956287HCID 18956287, compound

Product 1

HCID 18956307HCID 18956307, compoundYield 133.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl chloroformate (3.7 g) was added slowly to a suspension of 2-amino-4-(6-aminomethylpyridin-2-yl)thiazole trihydrochloride (8.9 g) and triethylamine (11.4 g) in N,N-dimethylformamide (80 ml) and tetrahydrofuran (80 ml) with cooling on an ice bath. The mixture was stirred with cooling for 1.5 hours and then at room temperature for 1 hours. The solvent was removed under reduced pressure. The residue was dissolved in water (300 ml). The mixture was alkalized with a saturated aqueous potassium carbonate solution and then was extracted with a mixture of ethyl acetate (500 ml) and tetrahydrofuran (100 ml). The extract was dried over magnesium sulfate and then was evaporated to afford 2-amino-4-(6-ethoxycarbonylaminomethylpyridin-2-yl)thiazole (10.51 g).

Workup

  1. temperaturewith cooling on an ice bath
  2. temperaturewith cooling for 1.5 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in water (300 ml)
  5. extractionwas extracted with a mixture of ethyl acetate (500 ml) and tetrahydrofuran (100 ml)
  6. dry with materialThe extract was dried over magnesium sulfate
  7. customwas evaporated

Sources & evidence

ORD record
ord-a73c2002720f417c9a9322b02e516c1b
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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