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

HRID 1254972Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-(2-chloro-3-difluoromethyl-phenoxy)-butyronitrile (300 mg, 1.2 mmol), ethylene diamine (0.33 ml, 4.9 mmol) and sodium tetrasulfide (11 mg, 0.1 mmol) was stirred for 2 hrs at 50° C., then cooled to room temperature. Cold water (0° C.) was added to the reaction mixture. The resultant suspension was stirred for ca 15 minutes and then filtered, washed and dried to yield 2-[1-(2-chloro-3-difluoromethyl-phenoxy)-propyl]-4,5-dihydro-1H-imidazole (m.p. 96-97° C.); 1H-NMR (D6-DMSO) 1.0, t, 3H, 1.8-2.0 m, 2H; 3.42 vbr s, 4H, 4.8, dd, 1H, 6.51, br s, 1H, 7.2, t, 1H, 7.25, d, 1H, 7.32, d, 1H, 7.43, t, 1H.

Workup

temperaturecooled to room temperature
filtrationfiltered
washwashed
customdried

Sources & evidence

ORD record: ord-0535d50c2df74d82a15ad7a9225c39d5
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455663B2

Reaction notes

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