Triethylamine → HCID 86742011, compound

HRID 1199537Notes

Reaction equation

HRID 1199537 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:9]2[CH:13]=[N:12][N:11]=[N:10]2)=[CH:4][C:3]=1I.[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[CH:16]=[CH2:17].C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:9]2[CH:13]=[N:12][N:11]=[N:10]2)=[CH:4][C:3]=1/[CH:17]=[CH:16]/[C:15]([O:19][CH2:20][CH3:21])=[O:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 19867064HCID 19867064, compound

Product 1

HCID 86742011HCID 86742011, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(4-amino-3-iodo-5-methylphenyl)tetrazole (5 g) in acetonitrile (80 cm3) was added ethyl acrylate (2 g), triethylamine (2 g) and palladium acetate (0.1 g). The mixture was heated under reflux for 11/2 hours, cooled and then partitioned between water (100 cm3) and dichloromethane (100 cm3). The aqueous phase was re-extracted with more dichloromethane (100 cm3) and the combined organic phases were dried (MgSO4), filtered and evaporated in vacuo. The residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with dichloromethane: methanol, 20:1. Combination and evaporation of appropriate fractions gave a solid which on recrystallisation from ethyl acetate/methanol afforded yellow needles of trans-ethyl 3-(2-amino-3-methyl-5-[tetrazol-1-yl]phenyl)prop-2-enoate, m.p. 210°-211°, (3.45 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 11/2 hours
  3. temperaturecooled
  4. custompartitioned between water (100 cm3) and dichloromethane (100 cm3)
  5. extractionThe aqueous phase was re-extracted with more dichloromethane (100 cm3)
  6. dry with materialthe combined organic phases were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  10. washeluting with dichloromethane
  11. customCombination and evaporation of appropriate fractions
  12. customgave a solid which
  13. customon recrystallisation from ethyl acetate/methanol afforded yellow needles of trans-ethyl 3-(2-amino-3-methyl-5-[tetrazol-1-yl]phenyl)prop-2-enoate, m.p. 210°-211°, (3.45 g)

Sources & evidence

ORD record
ord-24227376e50f4e4d865e646db66a2a8b
Source dataset
uspto-grants-1990_02
Patent number
US04900839

Reaction notes

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