5-Acenaphthyl cyanamide → HCID 178479314, compound

HRID 1457169Notes

Reaction equation

[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[C:6]([NH:13][C:14]#[N:15])=[CH:5][CH:4]=[C:3]3[CH2:2]1.[ClH:16].[Cl:17][C:18]1[C:24]([Cl:25])=[C:23]([Cl:26])[CH:22]=[CH:21][C:19]=1[NH2:20]>ClC1C=CC=CC=1>[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[C:6]([NH:13][C:14]([NH:20][C:19]2[CH:21]=[CH:22][C:23]([Cl:26])=[C:24]([Cl:25])[C:18]=2[Cl:17])=[NH:15])=[CH:5][CH:4]=[C:3]3[CH2:2]1.[ClH:16]

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 5-acenaphthyl cyanamide (0.194 g, 1 mmol) and 2,3,4-trichloroaniline hydrochloride (0.221 g, 0.95 mmol; prepared from 2,3,4-trichloroaniline and 1. ON HCl-ether) were heated at reflux in 5 mL of chlorobenzene. Shortly after reflux temperature was reached all the solids had dissolved to give a clear solution. After a total of 2 hour reflux, the mixture was cooled to 20° C. and allowed to stand for 24 hours. The solid was collected by filtration and washed with excess of methylene chloride and dried in vacuo at 40° C. to give product (0.293 g, 68%) as an off white solid, mp: 208°-10° C.; 1H NMR (CD3OD): δ 7.70-7.58 (m, 3H, Ar--H), 7.48 (d, 2H, J=7.5Hz, Ar--H), 3.47-3.41 (m, 4H, 2×CH2); HRMS 389.0220 (389.0253 calcd. for C19H14N3Cl3); Anal Calcd. for C19H15N3CI4 (427.15): C, 53.42; H, 3.54; N, 9.84; Cl, 33.2; Found: C, 53.25: H, 3.57; N, 9.67; Cl, 33.75.

Workup

temperaturewere heated
temperatureShortly after reflux temperature
dissolutionhad dissolved
customto give a clear solution
temperatureAfter a total of 2 hour reflux
filtrationThe solid was collected by filtration
washwashed with excess of methylene chloride
customdried in vacuo at 40° C.

Sources & evidence

ORD record: ord-a6e2ccff1e1a4a41996f73872ea5985b
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05847006

Reaction notes

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