Triethylamine → HCID 21910787, compound

HRID 1786642Notes

Reaction equation

HRID 1786642 reaction equation
[C:1]([OH:8])(=O)/[CH:2]=[CH:3]/[C:4](O)=[O:5].C([N:11]([CH2:14][CH3:15])CC)C.ClC(O[CH2:20][CH:21]([CH3:23])[CH3:22])=O.[CH2:24]([NH2:34])/[CH:25]=[C:26](/[CH2:28][CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])\[CH3:27]>O.O1CCCC1>[CH2:24]([NH:34][C:1](=[O:8])/[CH:2]=[CH:3]/[C:4]([NH:11][CH2:14]/[CH:15]=[C:2](/[CH2:3][CH2:4][CH:20]=[C:21]([CH3:23])[CH3:22])\[CH3:1])=[O:5])/[CH:25]=[C:26](/[CH2:28][CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])\[CH3:27]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 444972Fumaric AcidHCID 5475462Geranylamine

Product 1

HCID 21910787HCID 21910787, compoundYield 110.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a tetrahydrofuran (THF) (20 ml) solution containing fumaric acid (0.58 g, 5 mmols), triethylamine (1.01 g, 10 mmols) was added and the solution was cooled to 0° C., into which a THF (5 ml) solution containing isobutyl chloroformate (1.53 g, 10 mmols) was added dropwise. As the addition was continued, white precipitate started to form. After 30 minutes' stirring at 0° C., a THF (5 ml) solution containing geranylamine (1.53 g, 10 mmols) was added dropwise into the system, followed by an hour's stirring at 0° C. and further 4 hours' stirring at room temperature. After termination of the reaction, 50 ml of water was added to the reaction mixture which was then extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate. Filtering the magnesium sulfate off, the chloroform layer was condensed to provide a white crystal. Recrystallizing the same from ethanol, 1.07 g of the title compound was obtained. The yield was 55%.

Workup

  1. additionwas added
  2. additionwas added dropwise
  3. additionAs the addition
  4. customto form
  5. additionwas added dropwise into the system
  6. waitfollowed by an hour
  7. stirring's stirring at 0° C. and further 4 hours'
  8. stirringstirring at room temperature
  9. additionwas added to the reaction mixture which
  10. extractionwas then extracted with chloroform
  11. washThe chloroform layer was washed with water
  12. dry with materialdried over magnesium sulfate
  13. filtrationFiltering the magnesium sulfate off, the chloroform layer
  14. customcondensed
  15. customto provide a white crystal
  16. customRecrystallizing the same from ethanol

Sources & evidence

ORD record
ord-d5316dfe55c3453a90a3327d5fe4fda0
Source dataset
uspto-grants-2009_03
Patent number
US07507765B2

Reaction notes

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