HCID 86601266, compound → HCID 68889098, compound

HRID 853073Notes

Reaction equation

HRID 853073 reaction equation
[CH2:1]([O:3][C:4](=[O:18])/[C:5](/[N:15]=[N+]=[N-])=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([F:14])[CH:8]=1)[CH3:2]>CC1C=CC(C)=CC=1>[CH2:1]([O:3][C:4]([C:5]1[NH:15][C:12]2[C:7]([CH:6]=1)=[CH:8][C:9]([F:14])=[C:10]([CH3:13])[CH:11]=2)=[O:18])[CH3:2]

Participants

3

Reactant 1

HCID 86601266HCID 86601266, compound

Product 1

HCID 68889098HCID 68889098, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Conditions

Temperature
15 °C

Procedure

(Z)-2-Azido-3-(3-fluoro-4-methyl-phenyl)-acrylic acid ethyl ester (9.7 g, 0.039 mol) was dissolved in 80 ml p-xylene and divided into four portions which were refluxed for 1 h. The oil bath was removed and the yellow solutions were cooled to 15° C. The resulting suspensions were filtered, washed with n-hexane and the solid material collected. The combined mother liquors were evaporated and the resulting oil was purified on silical gel (0.030–0.063 mm) with n-hexane/tert-butyl methyl ether (50/1) as eluent. The purified fractions together with the first precipitates were combined and chromatographed again to yield the desired product as a colorless solid (3.2 g, 37.2%). EI-MS: m/e=249.1 (M).

Workup

  1. temperaturewere refluxed for 1 h
  2. customThe oil bath was removed
  3. filtrationThe resulting suspensions were filtered
  4. washwashed with n-hexane
  5. customthe solid material collected
  6. customThe combined mother liquors were evaporated
  7. customthe resulting oil was purified on silical gel (0.030–0.063 mm) with n-hexane/tert-butyl methyl ether (50/1) as eluent
  8. customThe purified fractions together with the first precipitates
  9. customchromatographed again

Sources & evidence

ORD record
ord-b0f912c2b2e44ac5b3bced5835bf6417
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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