Triethylamine → HCID 15022287, compound

HRID 1653659Notes

Reaction equation

HRID 1653659 reaction equation
C(N(CC)CC)C.Br[CH2:9][CH:10]=[CH:11][CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1.[OH:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].CN1CCCC1=O>O>[F:20][C:17]1[CH:18]=[CH:19][C:14](/[CH:13]=[CH:12]/[CH:11]=[CH:10]/[CH2:9][O:21][N:22]2[C:23](=[O:32])[C:24]3=[CH:31][CH:30]=[CH:29][CH:28]=[C:25]3[C:26]2=[O:27])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 13387N-methyl-2-pyrrolidoneHCID 54135450HCID 54135450, compound

Product 1

HCID 15022287HCID 15022287, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.3 ml (60 mmol ) of triethylamine were added dropwise at about 20° C. to a mixture of 10.4 g (43 mmol) of 1-bromo-5- (4-fluorophenyl)-2,4-pentadiene, 9.8 g (60 mmol) of N-hydroxyphthalimide and 45 ml of N-methyl-pyrrolidone. The mixture was stirred for 24 hours and then poured into 200 ml of water and extracted several times with ethyl acetate, after which the combined organic phases were washed with 5% by weight aqueous sodium hydroxide solution and then with saturated aqueous sodium chloride solution. After drying with magnesium sulfate and removal of the solvent, the residue was recrystallized from 70 ml of ethanol. Yield: 57%. Melting point: 155°-157° C.

Workup

  1. extractionextracted several times with ethyl acetate
  2. washafter which the combined organic phases were washed with 5% by weight aqueous sodium hydroxide solution
  3. dry with materialAfter drying with magnesium sulfate and removal of the solvent
  4. customthe residue was recrystallized from 70 ml of ethanol

Sources & evidence

ORD record
ord-374254abd27c4f7a947542b968464a07
Source dataset
uspto-grants-1995_04
Patent number
US05403812

Reaction notes

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