Water → HCID 159518958、化合物

HRID 2217129ノート

反応式

HRID 2217129 の反応式
[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]

参加物

6

反応物 4

HCID 962WaterHCID 24408BromineHCID 308355910H-PhenoselenazineHCID 159425053HCID 159425053、化合物

生成物 1

HCID 159518958HCID 159518958、化合物収率 17%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2c8b78486dca44619b6ddeb0c0a57e06
出典データセット
uspto-grants-2008_08
特許番号
US07407948B2

反応ノート

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