Triphenylphosphine → HCID 19019367, compound

HRID 2081673Notes

Reaction equation

HRID 2081673 reaction equation
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:22]([N:29]1[CH:34]=[C:33]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[C:32](=[O:54])[CH:31]=[C:30]1[CH2:55]O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[BrH:1].[CH2:22]([N:29]1[CH:34]=[C:33]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[C:32](=[O:54])[CH:31]=[C:30]1[CH2:55][Br:1])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 14749919HCID 14749919, compound

Product 1

HCID 19019367HCID 19019367, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5.1 mL (0.1 mole) Bromine are added dropwise at ambient temperature, while stirring, to a solution of 26.5 g (0.1 mole) triphenylphosphine in 600 mL anhydrous toluene, a white crystalline precipitate thereby being formed. After further stirring for 20 minutes at ambient temperature, 48.17 g (0.1 mole) 1-benzyl-2-hydroxymethyl-5-octadecyloxy-4(1H)-pyridone are added thereto in portions. Thereafter, the reaction mixture is stirred for 2 hours at 70° C., cooled and the precipitated product is filtered off, washed with toluene, dried and recrystallized from propan-2-ol, pale beige crystals being obtained; m.p. 92°-95° C.

Workup

  1. customa white crystalline precipitate thereby being formed
  2. stirringThereafter, the reaction mixture is stirred for 2 hours at 70° C.
  3. temperaturecooled
  4. filtrationthe precipitated product is filtered off
  5. washwashed with toluene
  6. customdried
  7. customrecrystallized from propan-2-ol, pale beige crystals
  8. custombeing obtained

Sources & evidence

ORD record
ord-a305a4b5a89b429084d28fa665948a59
Source dataset
uspto-grants-1993_02
Patent number
US05185352

Reaction notes

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