2-Aminobiphenyl → HCID 178477938, compound

HRID 461044Notes

Reaction equation

HRID 461044 reaction equation
[C:1]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][NH:2]1.P(Cl)(Cl)([Cl:17])=O.[C:20]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]([NH2:26])=[CH:22][CH:23]=[CH:24][CH:25]=1>C1C=CC=CC=1>[ClH:17].[C:20]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]=[C:1]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][NH:2]1

Participants

5

Reactant 3

HCID 70152-AminobiphenylHCID 13690LaurolactamHCID 24813Phosphorus oxychloride

Product 1

HCID 178477938HCID 178477938, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 43.5 g (0.22 mole) of 2-azacyclotridecanone in 200 ml of dry benzene is added dropwise 30.7 g (0.2 mole) of phosphorousoxychloride. The reaction mixture is stirred at room temperature for 4 hours after which 33.8 g (0.2 mole) of o-biphenylamine is added and stirring is continued at room temperature for 1 hour then at reflux temperature for 4 hours. The reaction mixture is alowed to stand overnight then is washed with 2N hydrochloric acid, dried and evaporated leaving a residue which is recrystallized from acetone/methanol to give 2-(o-biphenylylimino)azacyclotridecane hydrochloride, M.P. 249°-251° C.

Workup

  1. additionis added
  2. temperatureat reflux temperature for 4 hours
  3. waitto stand overnight
  4. washthen is washed with 2N hydrochloric acid
  5. customdried
  6. customevaporated
  7. customleaving a residue which
  8. customis recrystallized from acetone/methanol

Sources & evidence

ORD record
ord-08cad11378394902a85b01b2d6c19bcc
Source dataset
uspto-grants-1977_12
Patent number
US04061746

Reaction notes

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