1-Naphthalenamine, hydrochloride (1:1) → HCID 178436383, compound

HRID 257664

Reaction equation

HRID 257664 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([N:9]([CH3:12])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2].[ClH:13].[NH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1>ClCCl>[ClH:13].[C:15]1([NH:14][C:10]([N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=2)[CH3:12])=[NH:11])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 110941-Naphthalenamine, hydrochloride (1:1)HCID 10103434m-ethylphenyl-N-methylcyanamide

Product 1

HCID 178436383HCID 178436383, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of m-ethylphenyl-N-methylcyanamide (520 mg, 3.25 mmol) and 1-aminonaphthalene hydrochloride (508 mg, 3.25 mmol) was placed in a preheated oil bath at 160° C. for 3 hours and then allowed to cool to room temperature. The resulting solid was taken into dichloromethane and washed with 10% NAOH solution. The organic layer was concentrated and the resulting residue was dissolved in abs. ETOH (2 ml) and treated with dil. HCl. It was concentrated and the solid was twice recrystallized from abs. EtOH-Et2O to give N-(1-naphthyl)-N'-(m-ethylphenyl)-N'-methylguanidine hydrochloride (403 mg, 37%) as off-white needles. mp 223°-25° C.

Workup

  1. washwashed with 10% NAOH solution
  2. concentrationThe organic layer was concentrated
  3. dissolutionthe resulting residue was dissolved in abs
  4. additionETOH (2 ml) and treated with dil. HCl
  5. concentrationIt was concentrated
  6. customthe solid was twice recrystallized from abs

Sources & evidence

ORD record
ord-37ebb71bf1b94d0992fdb100f4beb874
Source dataset
uspto-grants-1993_11
Patent number
US05262568

Linked notes

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