Triethylamine → HCID 66629536, compound

HRID 406330Notes

Reaction equation

HRID 406330 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]([C:10]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[C:13]([O:19][CH3:20])=[CH:12][C:11]=1[CH3:21])[C:6]([NH:8][NH2:9])=O.[N:22]#[C:23][NH2:24].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C(O)C>[CH:16]([C:14]1[C:13]([O:19][CH3:20])=[CH:12][C:11]([CH3:21])=[C:10]([CH:5]2[CH2:4][CH2:3][CH2:2][N:8]3[N:9]=[C:23]([NH2:24])[N:22]=[C:6]23)[CH:15]=1)([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9864CyanamideHCID 521998p-Toluenesulfonic acid monohydrateHCID 66618852HCID 66618852, compound

Product 1

HCID 66629536HCID 66629536, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

5-Chloro-2-(5-isopropyl-4-methoxy-2-methylphenyl)pentanoic acid hydrazide (4.4 g) and cyanamide (3.6 g) were dissolved in ethanol (150 mL). p-Toluenesulfonic acid monohydrate (4 g) was added and the mixture was heated under reflux at 80° C. for two hours. After cooling to room temperature, triethylamine (9.8 mL) was added and the mixture was further heated under reflux at 80° C. for three days. The reaction solution was concentrated under reduced pressure. A sodium bicarbonate solution and ethyl acetate were added and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (2.4 g). The property values of the compound are as follows.

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling to room temperature
  3. temperaturethe mixture was further heated
  4. temperatureunder reflux at 80° C. for three days
  5. concentrationThe reaction solution was concentrated under reduced pressure
  6. additionA sodium bicarbonate solution and ethyl acetate were added
  7. customthe organic layer was separated
  8. washThe resulting organic layer was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe drying agent was separated by filtration
  11. concentrationthe organic layer was concentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-436d51027d5945a683abe2aacc647845
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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