Ethylenediamine → 2-[1-(2-methyl-3-trifluoromethyl-phenoxy)-propyl]-4,5-dihydro-1H-imidazole

HRID 455323Notes

Reaction equation

[CH3:1][C:2]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][C:3]=1[O:4][CH:5]([CH2:8][CH3:9])[C:6]#[N:7].[CH2:18](N)[CH2:19][NH2:20].[S-]SS[S-].[Na+].[Na+]>O>[CH3:1][C:2]1[C:13]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:11]=[CH:10][C:3]=1[O:4][CH:5]([C:6]1[NH:20][CH2:19][CH2:18][N:7]=1)[CH2:8][CH3:9]

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 2-(2-methyl-3-trifluoromethyl-phenoxy)-butyronitrile (192 mg, 0.790 mmol), ethylene diamine (0.216 ml, 3.16 mmol) and sodium tetrasulfide (7 mg, 0.04 mmol) was stirred for 4 hrs at 75° C., then cooled and stirred with water (ca 6 ml). The solid was filtered off, washed with water and dried in a vacuum to yield 2-[1-(2-methyl-3-trifluoromethyl-phenoxy)-propyl]-4,5-dihydro-1H-imidazole (m.p. 120-122° C.).

Workup

temperaturecooled
filtrationThe solid was filtered off
washwashed with water
customdried in a vacuum

Sources & evidence

ORD record: ord-242a11c404894fa784ce4ec07efa4bcc
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497293B2

Reaction notes

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