Phthalimide → 2',5-Dichloro-2-[2-(phthalimidomethyl)imidazol-1-yl]benzophenone

HRID 267432Notes

Reaction equation

HRID 267432 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:23])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH2:21]O.[C:24]1(=[O:34])[NH:28][C:27](=[O:29])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:23])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH2:21][N:28]1[C:24](=[O:34])[C:25]2=[CH:33][CH:32]=[CH:31][CH:30]=[C:26]2[C:27]1=[O:29]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 215558792',5-Dichloro-2-[2-(hydroxymethyl)imidazol-1-yl]benzophenone

Product 1

HCID 215559152',5-Dichloro-2-[2-(phthalimidomethyl)imidazol-1-yl]benzophenone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the manner given in Example 17, 3.47 g. (20.0 mmol) of 2',5-dichloro-2-[2-(hydroxymethyl)imidazol-1-yl]benzophenone is treated with 3.24 g. (22.0 mmol) of phthalimide and 5.76 g. (22.0 mmol) of triphenylphosphine suspended in 200 ml. of cold (0°-5°) tetrahydrofuran and finally with 3.83 g. (22.0 mmol) of diethyl azodicarboxylate, added slowly over three-fourths hour. After overnight stirring, the resulting solid is filtered and crystallized to afford 2',5-dichloro-2-[2-(phthalimidomethyl)imidazol-1-yl]benzophenone.

Workup

  1. filtrationthe resulting solid is filtered
  2. customcrystallized

Sources & evidence

ORD record
ord-fe9ad194a20245c1b8a0effb38a0d96a
Source dataset
uspto-grants-1976_03
Patent number
US03941803

Reaction notes

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