Hydrochloric Acid → HCID 22218673, compound

HRID 1795673Notes

Reaction equation

HRID 1795673 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.N1C=CC=CC=1.[C:19](Cl)(=[O:30])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH2:29].Cl>O.C1(C)C=CC=CC=1>[C:19]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH:9]=[CH:10][CH:11]=[CH:12]1)(=[O:30])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH2:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 3804210-Undecenoyl chlorideHCID 134196986-(1H-Pyrrol-1-yl)hexan-1-ol

Product 1

HCID 22218673HCID 22218673, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

62.0 g (0.371 mol) of N-(6-hydroxyhexyl)-pyrrole, 33.2 g (0.420 mol) of dry pyridine, and 1850 ml of dry toluene were put in a 2-liter reactor, and 300 ml of a dry toluene solution of 75.7 g (0.373 mol) of 10-undecenoylchloride was dropped thereto at 20° C. or below. The dropping time was 30 minutes. Thereafter, the mixture was stirred at the same temperature for one hour. The reaction mixture was poured into 1.5 liter of iced water, and was made acidic with use of 1N hydrochloric acid. It was subjected to ethyl acetate extraction, an organic layer was washed with water and concentrated brine and was dried using anhydrous magnesium sulfate, and the solvent was removed. As a result, 128.2 g of crude substance was obtained. This was subjected to purification by silicagel column with use of n-hexane/acetone=20/1, whereby 99.6 g of N-[6-(10-undecenoyloxy)hexyl]-pyrrole was obtained. The yield was 80.1%. The reaction of the step 4 is expressed by a reaction formula (15) shown below:

Workup

  1. customat 20° C. or below
  2. extractionIt was subjected to ethyl acetate extraction
  3. washan organic layer was washed with water and concentrated brine
  4. customwas dried
  5. customthe solvent was removed
  6. customAs a result, 128.2 g of crude substance was obtained
  7. customThis was subjected to purification by silicagel column with use of n-hexane/acetone=20/1

Sources & evidence

ORD record
ord-c92c128368cb45ca9fd938a11206964d
Source dataset
uspto-grants-2006_04
Patent number
US07027327B2

Reaction notes

Loading…