HCID 12295945, compound → HCID 178511987, compound

HRID 2371591Notes

Reaction equation

HRID 2371591 reaction equation
[C:1]1([NH:11][C:12]#[N:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[I:15][C:16]1[CH:28]=[CH:27][CH:26]=[CH:25][C:17]=1[NH:18]C1C=CC=CC=1>ClC1C=CC=CC=1>[C:1]1([NH:11][C:12]([NH:18][C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[I:15])=[NH:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 12295945HCID 12295945, compoundHCID 70061414HCID 70061414, compound

Product 1

HCID 178511987HCID 178511987, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 1-naphthylcyanamide (182 mg, 1.08 mmol) and o-iodophenylaniline hydrochloride (279 mg, 1.09 mmol) in chlorobenzene (5 ml) was heated at 135°-140° C. for 14 hours. It was concentrated and the residue was partitioned between dichloromethane and 10% NaOH solution. The organic layer was dried over Na2SO4 and concentrated. The resulting light green residue was recrystallized from 95% EtOH-H2O to give N-(1-naphthyl)-N'-(o-iodophenyl)-guanidine (140 mg, 33%) as off-white needles. mp 154°-155° C.

Workup

  1. concentrationIt was concentrated
  2. customthe residue was partitioned between dichloromethane and 10% NaOH solution
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting light green residue was recrystallized from 95% EtOH-H2O

Sources & evidence

ORD record
ord-11be484984f7423eb19011f2453cde13
Source dataset
uspto-grants-1992_03
Patent number
US05093525

Reaction notes

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