Triethylamine → 1,4-Bis(4-nitrophenyl)butane-1,4-diyl dimethanesulfonate

HRID 1470913

反応式

HRID 1470913 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:24])[CH2:11][CH2:12][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34].[NH4+].[Cl-]>C(Cl)Cl>[CH3:32][S:33]([O:14][CH:13]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[CH2:12][CH2:11][CH:10]([O:24][S:33]([CH3:32])(=[O:35])=[O:34])[C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)(=[O:35])=[O:34]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 59616924(1R,4R)-1,4-bis(4-nitrophenyl)butane-1,4-diol

生成物 1

HCID 596171791,4-Bis(4-nitrophenyl)butane-1,4-diyl dimethanesulfonate収率 64%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of the product from Example 1B (0.80 g, 2.407 mmol) in dry CH2Cl2 (25 ml) at 0° C. was added triethylamine (1.007 ml, 7.22 mmol), followed by dropwise addition of methanesulfonyl chloride (0.469 ml, 6.02 mmol). The resulting mixture was stirred at 0° C. for 30 min, during which time the starting material slowly went into solution. After stirring an additional 1 h at 0° C., a precipitate began to form. Saturated aq NH4Cl (4 ml) was added, and stirring was continued at room temperature for 20 min. The mixture was washed with water (2×10 ml), and the organic layer was treated with hexanes (10 ml) to give an orange solid that was collected by filtration to give the title compound (0.75 gm, 64% yield).

後処理

  1. stirringAfter stirring an additional 1 h at 0° C.
  2. customto form
  3. stirringstirring
  4. waitwas continued at room temperature for 20 min
  5. washThe mixture was washed with water (2×10 ml)
  6. additionthe organic layer was treated with hexanes (10 ml)
  7. customto give an orange solid
  8. filtrationthat was collected by filtration

出典と根拠

ORDレコード
ord-0b7f4742e0344cf98d52f500251aa39a
出典データセット
uspto-grants-2015_04
特許番号
US09006387B2

関連ノート

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