Phthalic Anhydride → 5-Bromopentylphthalimide

HRID 247201

Reaction equation

HRID 247201 reaction equation
C1(=O)OC(=O)C2=CC=CC=C12.NCCCCCO.O[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:35]=[CH:34][CH:33]=[C:27]2[C:28]([NH:30][C:31](=[O:32])[C:26]=12)=[O:29].P(Br)(Br)[Br:37]>C1(C)C=CC=CC=1.O>[Br:37][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:35]=[CH:34][CH:33]=[C:27]2[C:28]([NH:30][C:31](=[O:32])[C:26]=12)=[O:29]

Participants

7

Reactant 4

HCID 6811Phthalic AnhydrideHCID 24614Phosphorus tribromideHCID 756345-Aminopentan-1-olHCID 20161969HCID 20161969, compound

Product 1

HCID 223521765-Bromopentylphthalimide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
120 °C

Procedure

Phthalic anhydride (43.0 g, 0.29 mole) and 5-aminopentanol (29.9 g, 0.29 mole) in 250 ml dry toluene (dried over 4A sieves) were heated to reflux in a 120° C. oil bath with stirring for three hours. The system was equipped with a Dean-Stark trap for the azeotropic removal of water (5.3 ml). Upon TLC confirmation of complete formation of the intermediate, 5-hydroxypentylphthalimide (Rf =0.66 (A)), phosphorous tribromide (18.2 ml, 0.19 mole) in 20 ml dry toluene was added dropwise to the hot reaction mixture and the mixture was stirred for 1.5 hours at 100° C. After removal of an orange precipitate by filtration through a pad of Celite, the filtrate was concentrated by rotary evaporation, and the resulting oil was crystallized from absolute ethanol as white plates. Yield: 64.7 g (75.3%). Mp 59.5°-66.0° C. TLC: Rf =0.78 (A). MW calc. 295.10, found 295. Anal. calc. for C13H14NO2Br: C, 52.72; H, 4.76; N, 4.73; Br, 26.98. Found: C, 53.17; H, 4.91; N, 4.62; Br, 27.14. HPLC 100%. 1H NMR (CDCl3) 1.50 (2H, m), 1.72 (2H, m), 1.92 (2H, m), 3.40 (2H, t, 7 Hz), 3.70 (2H, t, 7 Hz), 7.72 (2H, m) and 7.90 (2H, m) for AA'BB"system.

Workup

  1. stirringthe mixture was stirred for 1.5 hours at 100° C
  2. customAfter removal of an orange precipitate
  3. filtrationby filtration through a pad of Celite
  4. concentrationthe filtrate was concentrated by rotary evaporation
  5. customthe resulting oil was crystallized from absolute ethanol as white plates

Sources & evidence

ORD record
ord-88ecf92a13d54143b83342c568420e18
Source dataset
uspto-grants-1987_11
Patent number
US04705892

Linked notes

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