Chloroform → HCID 68578627, compound

HRID 644796Notes

Reaction equation

HRID 644796 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[N:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1C.[CH:16](Cl)(Cl)Cl>C1(C)C=CC=CC=1>[Br-:1].[CH2:2]([N+:8]1[CH:9]=[CH:10][C:11]([CH3:16])=[CH:12][C:13]=1[CH3:14])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 79372,6-LutidineHCID 81011-Bromohexane

Product 1

HCID 68578627HCID 68578627, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Bromohexane (1 equivalent) was dissolved in some toluene in a round bottomed flask flushed with nitrogen. Then, lutidine (1 equivalent) was added and the mixture was heated to reflux. During the reaction, a brown product appeared. The reaction was stopped after 8 hours. Afterwards, the solvent was removed under the reduced pressure. A minimum amount of acetonitrile was added to dissolve the residue and ether was added to precipitate the product. The crude product was washed with ether to afford off-white crystals. The yield of the reaction is 83%. 1H NMR (CDCl3, 200 MHz): δ 0.89 (t, 3H), 1.26 (m), 1.85 (m), 2.64 (s, 3H), 2.93 (s, 3H), 4.81 (t, 2H), 7.75(d, 2H), 9.51 (d, 1H); IR (CHCl3, cm−1): 1398 (C═C), 1635 (C═N), 2975 (N—C).

Workup

  1. customflushed with nitrogen
  2. temperaturethe mixture was heated to reflux
  3. customDuring the reaction
  4. customAfterwards, the solvent was removed under the reduced pressure
  5. additionA minimum amount of acetonitrile was added
  6. dissolutionto dissolve the residue and ether
  7. additionwas added
  8. customto precipitate the product
  9. washThe crude product was washed with ether
  10. customto afford off-white crystals

Sources & evidence

ORD record
ord-6b8ec79325f64914976b52ff78a7241b
Source dataset
uspto-grants-2010_04
Patent number
US07700780B2

Reaction notes

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