Phthalimide → N-(20-Bromoeicosyl)phthalimide

HRID 1886744Notes

Reaction equation

HRID 1886744 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][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:42]1(=[O:52])[NH:46][C:45](=[O:47])[C:44]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]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][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:46]1[C:45](=[O:47])[C:44]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]2[C:42]1=[O:52]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 517665320-Bromoicosan-1-ol

Product 1

HCID 19698940N-(20-Bromoeicosyl)phthalimideYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following general procedure A, 69.4 mmol (26.2 g) of 20-Bromoeicosan-1-ol, 76.3 mmol (20.0 g) of triphenylphosphine, 76.3 mmol (11.2 g) of phthalimide and 76.3 mmol (15.5 mL) of diisopropyl azo dicarboxylate were reacted in 300 mL of tetrahydrofuran for 1 d and the mixture was processed accordingly. The crude product was purified by column chromatography (toluene). Yield 66%.

Workup

  1. customThe crude product was purified by column chromatography (toluene)

Sources & evidence

ORD record
ord-9dcc29fbdba84880a314def9c8443d3f
Source dataset
uspto-grants-2013_08
Patent number
US08501199B2

Reaction notes

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