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

HRID 482569

Reaction equation

HRID 482569 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 pre-heated 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-11d786a4e86342d0a91f37d44e0ef67d
Source dataset
uspto-grants-1998_08
Patent number
US05798390

Linked notes

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