Phthalimide → N-(12-Bromododecyl)phthalimide

HRID 1886743Notes

Reaction equation

HRID 1886743 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:34]1(=[O:44])[NH:38][C:37](=[O:39])[C:36]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:35]12.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:38]1[C:37](=[O:39])[C:36]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:35]2[C:34]1=[O:44]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 13789512-Bromo-1-dodecanol

Product 1

HCID 10763182N-(12-Bromododecyl)phthalimideYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following general procedure A, 70.0 mmol (18.6 g) of 12-Bromododecan-1-ol, 77.0 mmol (20.2 g) of triphenylphosphine, 77.0 mmol (11.3 g) of phthalimide and 77.0 mmol (16.1 mL) of diisopropyl azo dicarboxylate were reacted in 350 mL of tetrahydrofuran for 2.5 h and the mixture was processed accordingly. The crude product was purified by column chromatography (cyclohexane/ethyl acetate 9:1). Yield 93%.

Workup

  1. customThe crude product was purified by column chromatography (cyclohexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-b71fbd3aaf5f44f7b8931f466d2e2bce
Source dataset
uspto-grants-2013_08
Patent number
US08501199B2

Reaction notes

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