Water → HCID 159518958, compound

HRID 2217129Notes

Reaction equation

HRID 2217129 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[Se:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.BrBr.O.[Br-].[Br:19][C:20]1[CH:21]=[CH:22][C:23]2[NH:24][C:25]3[C:30]([SeH+]C=2C=1)=[CH:29][C:28](Br)=CC=3>C(O)(=O)C>[Br-:19].[CH2:12]([N:13]([C:3]1[CH:2]=[CH:1][C:14]2[NH:13][C:12]3[C:7]([SeH+:6][C:5]=2[CH:4]=1)=[CH:8][C:9]([N:24]([CH2:23][CH2:22][CH2:21][CH3:20])[CH2:25][CH2:30][CH2:29][CH3:28])=[CH:10][CH:11]=3)[CH2:14][CH2:5][CH2:4][CH3:3])[CH2:11][CH2:10][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 308355910H-PhenoselenazineHCID 159425053HCID 159425053, compound

Product 1

HCID 159518958HCID 159518958, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution of phenoselenazine (1.00 g) in glacial acetic acid (170 cm3), under nitrogen and cooled in an ice-bath was added a solution of bromine (10 cm3) in glacial acetic acid (10 cm3). After 10 minutes the reaction mixture was poured into rapidly stirred water (400 cm3). The resultant 3,7-dibromo-phenoselenazin-5-ylium bromide was deposited as a dark solid and was collected by filtration, washed with diethyl ether and dried. A portion of the product (1.24 g) was added to a vigorously stirred solution of dibutylamine (5.00 g) in dichloromethane (200 cm3) under an atmosphere of nitrogen. The reaction mixture was stirred for 18 hours and then washed successively with water, dilute aqueous hydrobromic acid (5% w/w) and finally water. The organic phase was dried (MgSO4) and the solvent removed by rotary evaporation. Flash column chromatography over silica gel 60 A was performed on the crude material using a mobile phase of chloroform with increasing methanol content to a maximum of 2%. 3,7-Bis-(N,N-dibutylamino)-phenoselenazin-5-ylium bromide was isolated as a dark blue solid in 17% yield.

Workup

  1. filtrationwas collected by filtration
  2. washwashed with diethyl ether
  3. customdried
  4. additionA portion of the product (1.24 g) was added to a vigorously stirred solution of dibutylamine (5.00 g) in dichloromethane (200 cm3) under an atmosphere of nitrogen
  5. washwashed successively with water, dilute aqueous hydrobromic acid (5% w/w) and finally water
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customthe solvent removed by rotary evaporation

Sources & evidence

ORD record
ord-2c8b78486dca44619b6ddeb0c0a57e06
Source dataset
uspto-grants-2008_08
Patent number
US07407948B2

Reaction notes

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