Triethylamine → HCID 160113003, compound

HRID 2217132Notes

Reaction equation

HRID 2217132 reaction equation
O.[I-].[I:3][C:4]1[CH:5]=[C+:6][C:7]2[NH:8][C:9]3[C:14]([Se:15][C:16]=2[CH:17]=1)=[CH:13][C:12](I)=[CH:11][CH:10]=3.[I-].C(N([C:27]1[CH:28]=[CH:29][C:30]2[NH:31][C:32]3[C:37]([SeH+][C:39]=2[CH:40]=1)=[CH:36][C:35](N(CCC)CCC)=[CH:34][CH:33]=3)CCC)CC.C(N(CC)CC)C.[CH2:55]([NH:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])[CH2:56][CH2:57][CH2:58][CH2:59][CH3:60]>CO>[I-:3].[CH2:62]([N:61]([C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([SeH+:15][C:16]=2[CH:17]=1)=[CH:13][C:12]([N:31]([CH2:30][CH2:29][CH2:28][CH2:27][CH2:40][CH3:39])[CH2:32][CH2:37][CH2:36][CH2:35][CH2:34][CH3:33])=[CH:11][CH:10]=3)[CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])[CH2:63][CH2:64][CH2:65][CH2:66][CH3:67]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8920DihexylamineHCID 86614462HCID 86614462, compoundHCID 161606724HCID 161606724, compound

Product 1

HCID 160113003HCID 160113003, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,7-diiodo-phenoselenazin-ylium iodide hydrate (2.34 g) (prepared as above for Compound 2) in methanol (300 cm3) was added triethylamine (1.0 cm3) followed by dihexylamine (5 cm3). The reaction was stirred for 24 hours. The residue remaining after removal of the methanol was taken up in dichloromethane and washed with dilute hydriodic acid (5% w/w) followed by water. The organic phase was isolated and dried (MgSO4). Flash column chromatography over silica gel 60 Å was performed on the crude material using a mobile phase of 85/15 methanol/water containing 3% w/v ammonium acetate. After isolation of the desired fractions and removal of the methanol, the product was extracted from the aqueous phase using dichloromethane. Concentration of the dichloromethane in vacuo and addition of an excess of diethyl ether resulted in precipitation of the product. The product was collected by filtration, washed with diethyl ether and dried to give 3,7-bis-(N,N-dihexylamino)-phenoselenazin-5-ylium iodide as a dark coloured powder, in 21% yield.

Workup

  1. customafter removal of the methanol
  2. washwashed with dilute hydriodic acid (5% w/w)
  3. customThe organic phase was isolated
  4. dry with materialdried (MgSO4)
  5. customAfter isolation of the desired fractions and removal of the methanol
  6. extractionthe product was extracted from the aqueous phase
  7. additionConcentration of the dichloromethane in vacuo and addition of an excess of diethyl ether
  8. customresulted in precipitation of the product
  9. filtrationThe product was collected by filtration
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-f5085a49d8934e768336802c8caade2a
Source dataset
uspto-grants-2008_08
Patent number
US07407948B2

Reaction notes

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