Triethylamine → HCID 66830885, compound

HRID 391164Notes

Reaction equation

HRID 391164 reaction equation
[I-].[CH3:2][N+:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[Br-:20].[C:21]([CH2:24][CH2:25][CH2:26][CH2:27][N+:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[S:30][C:29]=1[CH3:37])([OH:23])=[O:22].[Br-].CC1SC2C=CC=CC=2[NH+]=1>C(Cl)Cl>[Br-:20].[CH3:2][N+:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:37]=[C:29]2[N:28]([CH2:27][CH2:26][CH2:25][CH2:24][C:21]([OH:23])=[O:22])[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[S:30]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 19848Quinoline methiodide2×HCID 10544370HCID 10544370, compoundHCID 16237421HCID 16237421, compound

Product 1

HCID 66830885HCID 66830885, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Next, 1.36 g (5.0 mmol) of N-methylquinolinium iodide (Compound III) (FW 271.10), 7.0 mL (50 mmol) of triethylamine (FW 101.19, d=0.726), and 100 mL of methylene chloride were added to 3.24 g of mixture (crude product) containing Compound 112 (3-(4-carboxybutyl)-2-methylbenzothiazolium bromide) and 2-methylbenzothiazolium bromide. As a result, a transparent solution was obtained. This solution was stirred at 25° C. for 16 hours. Thereafter, the solvent was evaporated under reduced pressure. Acetone (200 mL) then was added to the residue and the precipitate obtained thereby was filtered, which then was washed with acetone. The residue thus obtained was dried under reduced pressure, and the red residue obtained after drying was washed with distilled water (50 mL). This further was filtered, which was washed with distilled water and then dried under reduced pressure. Thus a target substance (Compound 107) was obtained as red powder (654 mg, 1.39 mmol, 28%). This red powder was confirmed to be the target substance (Compound 107) through a comparison in 1HNMR spectrum with the reference value. Peak values from 1HNMR and 13CNMR (DMSO-d6) and the measured values of HRMS (ESI) are indicated below. Furthermore, FIG. 6 shows the 1HNMR spectrum (DMSO-d6) of Compound 107.

Workup

  1. customAs a result, a transparent solution was obtained
  2. customThereafter, the solvent was evaporated under reduced pressure
  3. additionAcetone (200 mL) then was added to the residue
  4. customthe precipitate obtained
  5. filtrationthereby was filtered
  6. washwhich then was washed with acetone
  7. customThe residue thus obtained
  8. customwas dried under reduced pressure
  9. customthe red residue obtained
  10. customafter drying
  11. washwas washed with distilled water (50 mL)
  12. filtrationThis further was filtered
  13. washwhich was washed with distilled water
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-f80d4fed1b464b8cb41a56eaf3f7bcd1
Source dataset
uspto-grants-2013_02
Patent number
US08383792B2

Reaction notes

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