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

HRID 1254972
Notes
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Reaction equation

HRID 1254972 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6101602CID 6101602HCID 595657802-(2-Chloro-3-difluoromethyl-phenoxy)-butyronitrile

Product 1

HCID 595657812-[1-(2-chloro-3-difluoromethyl-phenoxy)-propyl]-4,5-dihydro-1H-imidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washwashed
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes