Triethylamine → HCID 54533324, compound

HRID 1857475Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[N:18][C:19]#[N:20])OC2C=CC=CC=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][NH2:25].C(N(CC)CC)C>C(#N)C>[C:19]([NH:18][C:10]([NH:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1)=[N:25][CH2:24][C:23]1[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=1[Cl:21])#[N:20]

Participants

Conditions

Temperature: 82 °C

Procedure

To a solution of N-(3,5-dichlorophenyl)-N'-cyano-O-phenylisourea (0.8 mmol, 250 mg) in dry acetonitrile (2 ml), 2-chlorobenzylamine (0.9 mmol, 0.108 ml) and triethylamine (0.125 ml) were added. The mixture was stirred for 21/2 h at 82° C. under nitrogen. After concentration the residue was recrystallized from ethyl acetate to give the title compound (208 mg, 72%). Mp 186-187.5° C.; 1H-NMR (CDCl3): δ 4.54 (d, 2H), 5.53 (br, 1H), 7.15 (m, 2H), 7.3 (m, 3H), 7.4 (m, 2H), 7.75 ppm (br, 1H); EI SP/MS: 394 (M+). MA calc for C15H11C13N4 : C, 50.95%; H, 3.14%; N, 15.84%. Found: C, 50.68%; H, 3.10%; N, 15.49%.

Workup

concentrationAfter concentration the residue
customwas recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-707e4ff12aa04cfb92f331738385a5de
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147098

Reaction notes

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