Phenylacetonitrile → 2-Amino-5-iodobenzophenone

HRID 1768329Notes

Reaction equation

HRID 1768329 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][CH:3]=1.C1(CC#N)C=CC=CC=1.N[C:21]1[CH:34]=[CH:33][C:32](Cl)=[CH:31][C:22]=1[C:23](C1C=CC=CC=1)=[O:24].N1C2C=CC=CC=2C=CC=N1.C(OP(Cl)(=O)OCC)C.[H-].[Na+].[N+](CC(OCC)=O)#[C-]>>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][C:4]=1[C:23]([C:22]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:21]=1)=[O:24]

Participants

8

Reactant 7

HCID 8794PhenylacetonitrileHCID 124951-Iodo-4-nitrobenzeneHCID 128702-Amino-5-chlorobenzophenoneHCID 13139Diethyl chlorophosphateHCID 24758Sodium hydrideHCID 134664BenzodiazepineHCID 533707Ethyl isocyanoacetate

Product 1

HCID 129066402-Amino-5-iodobenzophenone

Procedure

2-Amino-5-iodo-benzophenone was prepared from p-iodonitrobenzene and phenylacetonitrile according to the literature.11 2-Amino-5-chloro-benzophenone was commercially available from Acros. The benzodiazepine 60 was reacted with diethylphosphorochloridate in the presence of sodium hydride, followed by the addition of ethyl isocyanoacetate to provide the ester 62 (Hz120), as shown in Scheme 13.

Sources & evidence

ORD record
ord-18aae5fca1ee482b80f5ecbce31a22bc
Source dataset
uspto-grants-2007_06
Patent number
US07235656B2

Reaction notes

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