Pyridinium chloride → HCID 22139449, compound

HRID 1825792Notes

Reaction equation

HRID 1825792 reaction equation
C([O:8][C:9]1[C:22]2[S:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][C:13]=2[C:12]([NH:23]CC2C=CC(OC)=CC=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.Cl.N1C=CC=CC=1>>[NH2:23][C:12]1[C:13]2[CH2:14][C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:21][C:22]=2[C:9]([OH:8])=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 22139447HCID 22139447, compound

Product 1

HCID 22139449HCID 22139449, compoundYield 99.1%

Conditions

Temperature
150 °C

Procedure

(4-Benzyloxy-9H-thioxanthen-1-yl)-(4-methoxy-benzyl)-amine (14.51 g, 33.00 mmol) was mixed thoroughly with solid pyridine hydrochloride (190 g, 165.00 mmol) before being heated to 150° C. and stirred at this temperature for a further 12 hours. Upon completion the reaction was cooled slightly before being poured into an beaker of ice/water. The brown precipitate was removed by filtration and the filtrate adjusted to pH 11 with NH3OH solution before being extracted with CH2Cl2 (3×100 ml). The combined organic phases were then washed with water (1×100 ml) and brine (1×100 ml) then dried using MgSO4, filtered and concentrated in vacuo to give the title compound as a thick brown oil (7.50 g, 99.1%) m/z (LC-MS, ESP): 229 [M+H]+, R/T=4.15 mins.

Workup

  1. temperatureUpon completion the reaction was cooled slightly
  2. customThe brown precipitate was removed by filtration
  3. extractionbefore being extracted with CH2Cl2 (3×100 ml)
  4. washThe combined organic phases were then washed with water (1×100 ml) and brine (1×100 ml)
  5. customthen dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8df563987c35466caa3aa1a9cb07280e
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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