Isoamylamine → HCID 11197309, compound

HRID 1857479Notes

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.[CH3:21][CH:22]([CH3:26])[CH2:23][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][CH2:23][CH:22]([CH3:26])[CH3:21])#[N:20]

Participants

Conditions

Temperature: 85 °C

Procedure

To N-(3,5-Dichlorophenyl)-N'-cyano-O-phenylisourea (0.98 mmol, 300 mg) in dry acetonitrile (2 ml), 3-methylbutylamine (2.16 mmol, 0.255 ml) and triethylamine (1.08 mmol, 0.150 ml) were added. The reaction mixture was stirred for 16 h at 85° C. under nitrogen. The precipitated material was filtered off and recrystallized from ethyl acetate to give the title compound (160 mg, 54%) as white crystals. Mp 146.5-1451.5° C.; 1H-NMR (CDCl3): δ 0.94 (d, 6H), 1.43 (q, 2H), 1.6 (m, 1H), 3.31 (q, 2H), 4.9 (br, 1H), 7.18 (br s, 2H), 7.29 (br s, 1H), 7.5 ppm (br, 1H); MA calc for C13H16Cl2N4 : C, 52.19%; H, 5.39%; N, 18.73%. Found: C, 52.23%; H, 5.51%; N, 18.60%.

Workup

filtrationThe precipitated material was filtered off
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-e2876621ba3044ad899581ad34d74af3
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06147098

Reaction notes

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