Triethylamine → HCID 13746018, compound

HRID 2290908Notes

Reaction equation

HRID 2290908 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]=[CH:9][C:10]([OH:12])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.Cl.[CH3:22][O:23][C:24]1[C:36]2[CH2:35][CH2:34][CH:33]3[CH:29]([CH2:30][NH:31][CH2:32]3)[C:28]=2[CH:27]=[CH:26][C:25]=1[O:37][CH3:38].C(N(CC)CC)C>C(Cl)Cl.O.C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH2:9][C:10]([N:31]2[CH2:30][CH:29]3[CH:33]([CH2:34][CH2:35][C:36]4[C:24]([O:23][CH3:22])=[C:25]([O:37][CH3:38])[CH:26]=[CH:27][C:28]=43)[CH2:32]2)=[O:12])=[CH:13][CH:14]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 701562-Propenoic acid, 3-(4-nitrophenyl)-HCID 20230765HCID 20230765, compound

Product 1

HCID 13746018HCID 13746018, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A slurry of p-nitrocinnamic acid (1.9 g, 9.8 mmole, Aldrich) and 22 mL dry benzene was stirred under N2 at 0° C. as oxalyl chloride (2.2 mL, 25.2 mmole) was added dropwise. The reaction mixture was stirred at reflux for 11/4 hr, was cooled to room temperature and evaporated. Benzene was added and evaporated several times. The acid chloride was dissolved in ca 15 mL CH2Cl2, and was added dropwise to a 0° C. solution of the compound of example 5 (free base, 1.9 g, 8.2 mmole) in 25 mL CH2Cl2, and triethylamine (1.6 mL, 11.5 mmole). The reaction mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture and the layers were separated. The aqueous layer was extracted twice with CH2Cl2. The combined organic layers were washed with 1N HCl, saturated aqueous NaHCO3, saturated aqueous NaCl, dried (MgSO 4), filtered, and evaporated (in-vacuo) to yield a tan solid which was triturated with Et2O to yield 2.68 g tan solid (80%); mp 231°-4°.

Workup

  1. additionwas added dropwise
  2. temperatureat reflux for 11/4 hr
  3. customevaporated
  4. additionBenzene was added
  5. customevaporated several times
  6. dissolutionThe acid chloride was dissolved in ca 15 mL CH2Cl2
  7. stirringThe reaction mixture was stirred at room temperature for 1 hour
  8. customthe layers were separated
  9. extractionThe aqueous layer was extracted twice with CH2Cl2
  10. washThe combined organic layers were washed with 1N HCl, saturated aqueous NaHCO3, saturated aqueous NaCl
  11. dry with materialdried (MgSO 4)
  12. filtrationfiltered
  13. customevaporated (in-vacuo)
  14. customto yield a tan solid which
  15. customwas triturated with Et2O

Sources & evidence

ORD record
ord-8cd5e01571f348eab5a082716687f74e
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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