Hydrochloric Acid → HCID 21289507, compound

HRID 868017Notes

Reaction equation

HRID 868017 reaction equation
N(OC(C)(C)C)=O.N[C:9]1[S:10][C:11]([CH2:14][CH2:15][CH:16]2[CH2:25][CH2:24][CH2:23][C:22]3[C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20][CH:19]=[CH:18][C:17]2=3)=[CH:12][N:13]=1.Cl>C(#N)C.C(O)(=O)C.[Zn]>[S:10]1[C:11]([CH2:14][CH2:15][CH:16]2[CH2:25][CH2:24][CH2:23][C:22]3[C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20][CH:19]=[CH:18][C:17]2=3)=[CH:12][N:13]=[CH:9]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 21289480HCID 21289480, compound

Product 1

HCID 21289507HCID 21289507, compoundYield 75.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent2×

Procedure

0.87 g of cupric chloride was suspended in 20 ml of acetonitrile and 0.82 g of tertiary butyl nitrite was added thereto. A solution of 1.8 g of ethyl 5-(2-(2-aminothiazole-5-yl)ethyl)-5,6,7,8-tetrahydro-1-naphthalenecarboxylate in 5 ml of acetonitrile was added dropwise to the mixture. After evolution of gas ceased, 15% hydrochloric acid was added to the mixture. The resulting mixture was extracted with chloroform. The extract was washed with water, dried and then concentrated in vacuo. The residue was purified by silica gel column chromatography with chloroform eluent to give an oily product. The product was dissolved in 30 ml of acetic acid, and a small amount of zinc powder was added thereto under refluxing. The above procedure was repeated four times at hourly intervals and the total amount of zinc was 0.4 g. The insoluble material was removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in chloroform. The solution was washed with water and dried and then concentrated in vacuo. The residue was purified by silica gel column chromatography to give 1.3 g of ethyl 5-(2-(5-thiazolyl)ethyl)-5,6,7,8-tetrahydro-1-naphthalenecarboxylate as an oil.

Workup

  1. extractionThe resulting mixture was extracted with chloroform
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography with chloroform eluent
  6. customto give an oily product
  7. temperatureunder refluxing
  8. customThe insoluble material was removed by filtration
  9. concentrationthe filtrate was concentrated in vacuo
  10. dissolutionThe residue was dissolved in chloroform
  11. washThe solution was washed with water
  12. customdried
  13. concentrationconcentrated in vacuo
  14. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f2f9fad06ef147ab8f13da08f122ae2b
Source dataset
uspto-grants-1988_10
Patent number
US04777257

Reaction notes

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