1-Naphthalenamine, hydrochloride (1:1) → HCID 178438973, compound

HRID 2371593Notes

Reaction equation

HRID 2371593 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]#[N:12])([CH3:3])[CH3:2].Cl.[C:14]1([NH2:24])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1>ClC1C=CC=CC=1.NC1C2C(=CC=CC=2)C=CC=1>[C:14]1([NH:24][C:11]([NH:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:1]([CH3:3])[CH3:2])=[NH:12])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 110941-Naphthalenamine, hydrochloride (1:1)HCID 10261376Cyanamide, [2-(1-methylethyl)phenyl]- (9CI)

Product 1

HCID 178438973HCID 178438973, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 86401-NaphthylamineCatalystHCID 7964ChlorobenzeneSolvent

Procedure

A solution of o-isopropylphenylcyanamide (1.13 g, 7.05 mmol), 1-naphthylamine hydrochloride (1.1 g, 7.04 mmol) and 1-aminonaphthalene (14.38 mg, 0.1 mmol) in chlorobenzene (20 ml) was heated to 150° C. for 4 hours and at room temperature for 10 hours. It was concentrated and the residue was partitioned between dichloromethane and 10% NaOH solution. The organic layer was concentrated and the resulting solid was recrystallized from EtOH - H2O (10:1) to give N-(1-naphthyl)-N'-(o-isopropylphenyl)guanidine (940 mg, 44%) as white crystals. mp 175°-177° C.

Workup

  1. concentrationIt was concentrated
  2. customthe residue was partitioned between dichloromethane and 10% NaOH solution
  3. concentrationThe organic layer was concentrated
  4. customthe resulting solid was recrystallized from EtOH - H2O (10:1)

Sources & evidence

ORD record
ord-865de062083c4d8782e1dc51d1160622
Source dataset
uspto-grants-1992_03
Patent number
US05093525

Reaction notes

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