Phthalimide → 5-(4-Nitrophenyl)-8-(phthalimidomethyl)-9H-1,3-dioxolo[4,5-h][2,3]-benzodiazepine

HRID 1359572Notes

Reaction equation

HRID 1359572 reaction equation
N(C(OCC)=O)=NC(OCC)=O.O[CH2:14][C:15]1[CH2:21][C:20]2[CH:22]=[C:23]3[O:28][CH2:27][O:26][C:24]3=[CH:25][C:19]=2[C:18]([C:29]2[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=2)=[N:17][N:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:57]1(=[O:67])[NH:61][C:60](=[O:62])[C:59]2=[CH:63][CH:64]=[CH:65][CH:66]=[C:58]12>C1COCC1>[N+:35]([C:32]1[CH:33]=[CH:34][C:29]([C:18]2[C:19]3[CH:25]=[C:24]4[O:26][CH2:27][O:28][C:23]4=[CH:22][C:20]=3[CH2:21][C:15]([CH2:14][N:61]3[C:60](=[O:62])[C:59]4=[CH:63][CH:64]=[CH:65][CH:66]=[C:58]4[C:57]3=[O:67])=[N:16][N:17]=2)=[CH:30][CH:31]=1)([O-:37])=[O:36]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 181831918-Hydroxymethyl-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine2×

Product 1

HCID 181831245-(4-Nitrophenyl)-8-(phthalimidomethyl)-9H-1,3-dioxolo[4,5-h][2,3]-benzodiazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.25 ml (8.05 mmol) of diethyl azodicarboxylate in 7 ml of THF is added in drops to a stirred solution of 2.60 g (7.66 mmol) of 8-hydroxymethyl-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h][2,3]-benzodiazepine (starting compound III.), 2.11 g (8.05 mmol) of triphenylphosphine and 1.18 g (8.05 mmol) of phthalimide in 130 ml of dry THF at room temperature. The mixture is stirred for 24 hours at this temperature. Then, the precipitated product is suctioned off and washed with ethanol. 2.87 g (80%) of the title compound, which can be further processed without further purification, is obtained.

Workup

  1. washwashed with ethanol
  2. custom2.87 g (80%) of the title compound, which can be further processed without further purification
  3. customis obtained

Sources & evidence

ORD record
ord-ccef06c579284bcdbc238ad1865a9f60
Source dataset
uspto-grants-2003_07
Patent number
US06600036B2

Reaction notes

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