Benzoyl chloride → 2-(N-benzoylimino)-4,4'-dinitrobiphenyl

HRID 1377008Notes

Reaction equation

HRID 1377008 reaction equation
NC1C=C([C:15]2[C:20]([C:21](N)=[O:22])=[CH:19][CH:18]=[CH:17][CH:16]=2)C(C2C=CC(N)=CC=2)=CC=1.[N+:24]([C:27]1[CH:28]=[C:29]([NH2:42])[C:30]([C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[CH:31][CH:32]=1)([O-:26])=[O:25].C(Cl)(=O)C1C=CC=CC=1>CN(C1C=CN=CC=1)C.CN1CCCC1=O>[C:21]([N:42]=[C:29]1[CH2:28][C:27]([N+:24]([O-:26])=[O:25])=[CH:32][CH:31]=[C:30]1[C:33]1[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=1)(=[O:22])[C:20]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 932654,4'-Dinitro(1,1'-biphenyl)-2-amineHCID 229190354,4'-Diaminobiphenyl-2-benzamide

Product 1

HCID 867512112-(N-benzoylimino)-4,4'-dinitrobiphenyl

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A method for preparing 4,4'-diaminobiphenyl-2-benzamide which consists essentially of the steps of reacting 4,4'-dinitro-2-biphenylamine with benzoyl chloride in the presence of 4-dimethylamine pyridine in N-methyl-2-pyrrolidinone (NMP) to give 2-(N-benzoylimino)-4,4'-dinitrobiphenyl, and hydrogenating said 2-(N-benzoylimino)-4,4:dinitrobiphenyl.

Sources & evidence

ORD record
ord-44ddf468f8a44c4eb2da60859a3102c8
Source dataset
uspto-grants-1997_09
Patent number
US05663437

Reaction notes

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