Ferrous Chloride → (1-{6-[1-(2-Butyl-phenylimino)-ethyl]-pyridin-2-yl}-ethylidene)-(2,6-dimethyl-phenyl)-amine iron (II) chloride

HRID 1406598Notes

Reaction equation

HRID 1406598 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]=[C:12]([C:14]1[N:19]=[C:18]([C:20](=[N:22][C:23]2[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:30])[CH3:21])[CH:17]=[CH:16][CH:15]=1)[CH3:13])[CH2:2][CH2:3][CH3:4].[Fe:31]([Cl:33])[Cl:32]>C1COCC1>[Fe:31]([Cl:33])[Cl:32].[CH2:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]=[C:12]([C:14]1[N:19]=[C:18]([C:20](=[N:22][C:23]2[C:24]([CH3:30])=[CH:25][CH:26]=[CH:27][C:28]=2[CH3:29])[CH3:21])[CH:17]=[CH:16][CH:15]=1)[CH3:13])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24458Ferrous ChlorideHCID 86674616(1-{6-[1-(2-Butyl-phenylimino)-ethyl]-pyridin-2-yl}-ethylidene)-(2,6-dimethyl-phenyl)-amine

Product 1

HCID 131732193(1-{6-[1-(2-Butyl-phenylimino)-ethyl]-pyridin-2-yl}-ethylidene)-(2,6-dimethyl-phenyl)-amine iron (II) chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.9 g (0.0048 mol) of (1-{6-[1-(2-n-Butyl-phenylimino)-ethyl]-pyridin-2-yl}-ethylidene)-(2,6-dimethyl-phenyl)-amine 11 (1.9 g, 0.0048 mol) was added in one portion to the suspension of 0.42 g (0.0033 mol) of iron (II) chloride in 40 ml of THF at ambient temperature under nitrogen glove box. The reaction mixture was stirred for 12 h. The resultant blue solid was filtered and washed by 50 ml of pentanes three times and dried under 1-mm vacuum overnight. The yield of (1-{6-[1-(2-n-butyl-phenylimino)-ethyl]-pyridin-2-yl}-ethylidene)-(2,6-dimethyl-phenyl)-amine iron (II) chloride 13 was 1.37 g (79%).

Workup

  1. filtrationThe resultant blue solid was filtered
  2. washwashed by 50 ml of pentanes three times
  3. customdried under 1-mm vacuum overnight

Sources & evidence

ORD record
ord-4e284c97a5164070820277a8a4c01c07
Source dataset
uspto-grants-2014_12
Patent number
US08916664B2

Reaction notes

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