Tetrahydrofuran → 2-chloro-5-nitrocinnamic acid-N-methyl-N-hexylamide

HRID 1085391

Reaction equation

HRID 1085391 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cl:9][C:10]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:11]=1[CH:12]=[CH:13][CH2:14]Cl.[O:23]1CCCC1>C(OCC)(=O)C>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:14](=[O:23])[CH:13]=[CH:12][C:11]1[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:10]=1[Cl:9]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 37079N-MethylhexylamineHCID 54271341HCID 54271341, compound

Product 1

HCID 537213752-chloro-5-nitrocinnamic acid-N-methyl-N-hexylamideYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

At 0° to 5° C., 11.5 g (0.10 mol) of N-methylhexylamine in 100 ml of tetrahydrofuran was added to a solution of 12.3 g (0.05 mol) of 2-chloro5-nitrocinnamyl chloride in 40 ml of tetrahydrofuran. After the mixture had been stirred for 2 hours, the solvent was removed, and the residue thus obtained was dissolved in ethyl acetate and extracted with 5% strength sodium hydroxide solution. The organic phase was washed with water, followed by separation and drying, to give 13.3 g (81% of theory) of 2-chloro-5-nitrocinnamic acid-N-methyl-N-hexylamide.

Workup

  1. customthe solvent was removed
  2. customthe residue thus obtained
  3. extractionextracted with 5% strength sodium hydroxide solution
  4. washThe organic phase was washed with water
  5. customfollowed by separation
  6. customdrying

Sources & evidence

ORD record
ord-6e5bbcb0cb1941e198c399ff15951cc1
Source dataset
uspto-grants-1991_04
Patent number
US05009701

Linked notes

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