Hydrochloric Acid → HCID 178425541, compound

HRID 1069175Notes

Reaction equation

[C:1]([N:3]([CH3:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[CH:5]=1)#[N:2].[C:12]1([NH2:22])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.Cl>>[C:12]1([NH:22][C:1]([N:3]([C:4]2[CH:5]=[C:6]([CH3:10])[CH:7]=[CH:8][CH:9]=2)[CH3:11])=[NH:2])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 86401-Naphthylamine

HCID 10261216N-cyano-N-methyl-3-toluidine

Product 1

HCID 178425541HCID 178425541, compound

Procedure

A mixture of N-cyano-N-methyl-3-toluidine (0.47 g, 3.22 mmol) and 1-naphthylamine.HCl (0.54 g, 3 mmol) in a 5 ml round bottom flask was heated in a preheated oil bath at 170-190° C. for 3 h under N2. The dark brown solution was allowed to cool to room temperature, and it became a rocky solid. The crude product was flash chromatographed on silica gel to yield N-(1-naphthyl)-N′-(m-tolyl)-N′-methylguanidine.HCl (40% yield) as a white powder. Elemental analysis: IR (CH2Cl2): 1625, 1600, 1560 cm−1. 1NMR (CDCl3): δ 2.135 (s, 3H), 3.536 (s, 3H), 6.847-7.972 (m, 11H). 13C-NMR (CDCl3): 20.9, 41.0, 122.6-141.6, 155.8. C19H20N3OCl.1/256 H2O. (Cacl.) C: 70.02%, H: 6.19%, N: 12.89%; (Found) C: 70.33%, H: 6.20%, N: 12.90%

Workup

customchromatographed on silica gel

Sources & evidence

ORD record: ord-d5dc29d7bb7e4b3291e8680c149a7a52
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06251948B1

Reaction notes

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