Diethyl Ether → HCID 11777289, compound

HRID 728164Notes

Reaction equation

HRID 728164 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11][CH2:12][C:13]3[N:14]=[CH:15][N:16](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:17]=3[CH3:18])[CH:8]=[CH:7][C:5]=2[N:6]=1.C(OCC)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11][CH2:12][C:13]3[N:14]=[CH:15][NH:16][C:17]=3[CH3:18])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 10413658HCID 10413658, compound

Product 1

HCID 11777289HCID 11777289, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A mixture of 2-amino-6-[2-(5-methyl-1-tritylimidazol-4-yl)ethyl]benzothiazole (1.4 g) in anisole (1.4 ml) and trifluoroacetic acid (6.0 ml) was stirred for 5 hours at ambient temperature. To the reaction mixture was added a diethyl ether, and precipitate was collected by filtration. To the precipitate was added a mixture of tetrahydrofuran, ethyl acetate and water and the mixture was adjusted to pH 9 with potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. Evaporation of a solvent gave a residue, which was purified by a column chromatography on alumina eluting with a mixture of chloroform and methanol (9:1, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo to give 2-amino-6-[2-(5-methylimidazol-4-yl)ethyl]benzothiazole (0.24 g).

Workup

  1. filtrationwas collected by filtration
  2. additionTo the precipitate was added
  3. additiona mixture of tetrahydrofuran, ethyl acetate and water
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of a solvent
  7. customgave a residue, which
  8. customwas purified by a column chromatography on alumina eluting with a mixture of chloroform and methanol (9:1, V/V)
  9. additionThe eluted fractions containing the desired product
  10. customwere collected
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-826f0544325d419dbaed13d17ceab702
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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