Hydrochloric Acid → HCID 53412023, compound

HRID 726293Notes

Reaction equation

HRID 726293 reaction equation
NC1C=CC(C=CC(OCC)=O)=CC=1.S(Cl)(C)(=O)=O.[S:20]([NH:24][C:25]1[CH:37]=[CH:36][C:28]([CH:29]=[CH:30][C:31]([O:33]CC)=[O:32])=[CH:27][CH:26]=1)([CH3:23])(=[O:22])=[O:21].S(N(C1C=CC(C=CC(OCC)=O)=CC=1)S(C)(=O)=O)(C)(=O)=O.[OH-].[Na+].Cl>C(Cl)Cl.C(O)C.O.C(N(CC)CC)C>[S:20]([NH:24][C:25]1[CH:37]=[CH:36][C:28]([CH:29]=[CH:30][C:31]([OH:33])=[O:32])=[CH:27][CH:26]=1)([CH3:23])(=[O:21])=[O:22]

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 97826Ethyl 3-(4-aminophenyl)acrylateHCID 54233064HCID 54233064, compoundHCID 54448829HCID 54448829, compound

Product 1

HCID 53412023HCID 53412023, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of ethyl 4-aminocinnamate (150 mg) and triethylamine (94 mg) in methylene chloride (3 ml) was added mesyl chloride (0.08 ml) under ice-cooling under nitrogen atmosphere, and the mixture was stirred at ambient temperature for 2 hours. The reaction mixture was poured into water, and extracted with methylene chloride twice. The combined organic layer was washed with water, dried over magnesium sulfate and concentrated to give a residue including ethyl 4-mesylaminocinnamate and ethyl 4-(N,N-dimesylamino)cinnamate. The residue was dissolved in ethanol, and 1N aqueous sodium hydroxide solution (1.5 ml) was added thereto at 40° C. The mixture was stirred at ambient temperature for 2 days, and 1N hydrochloric acid (1.5 ml) was added thereto. The mixture was concentrated in vacuo, and the residue was partitioned between 10% methanol-methylene chloride and water. The organic layer was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (methylene chloride-methanol, 10:1, V/V) to give 4-mesylaminocinnamic acid (49.3 mg).

Workup

  1. temperaturecooling under nitrogen atmosphere
  2. extractionextracted with methylene chloride twice
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give a residue
  7. customat 40° C
  8. stirringThe mixture was stirred at ambient temperature for 2 days
  9. concentrationThe mixture was concentrated in vacuo
  10. customthe residue was partitioned between 10% methanol-methylene chloride and water
  11. washThe organic layer was washed with water
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated in vacuo
  14. customThe residue was purified by preparative thin-layer chromatography (methylene chloride-methanol, 10:1, V/V)

Sources & evidence

ORD record
ord-d8624eefceb24d3da04e2f3dd7c28217
Source dataset
uspto-grants-1998_01
Patent number
US05708173

Reaction notes

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