1-Bromo-3-chloropropane → 3-(3-Chloropropyl)-5-nitrobenzo[d]oxazol-2(3H)-one

HRID 1688006

反応式

HRID 1688006 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[O:12])[NH:9][C:8]=2[CH:13]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][CH2:23][Cl:24]>CC(C)=O.O.CCOC(C)=O>[Cl:24][CH2:23][CH2:22][CH2:21][N:9]1[C:8]2[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[O:11][C:10]1=[O:12]

参加物

7

反応物 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 2639655-Nitro-2,3-dihydro-1,3-benzoxazol-2-one

生成物 1

HCID 434479093-(3-Chloropropyl)-5-nitrobenzo[d]oxazol-2(3H)-one

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
55 °C

実験手順

5-Nitro-3H-benzoxazol-2-one (5.35 g, 29.7 mmol) in Acetone (300 mL) was treated with Potassium carbonate (6.99 g, 50.6 mmol) then 1-Bromo-3-chloropropane (10.0 mL, 101 mmol) was added. After 45 min, the mixture was heated to 55° C. overnight. The reaction was cooled, diluted with 100 mL water and 150 mL EtOAc. The layers were separated, the org. washed with brine (50 mL), dried over sodium sulfate, filtered through a ½″h×2″w pad of SiO2 and conc. in vacuo. to near dryness. The oily remainder was suspended in 100 mL 5% EtOAc:Hexane, resulting in precipitation of the product. The solids were triturated for 2 h to break up the solids, collected by filtration and washed with hexane (2×60 mL). After drying, 3-(3-Chloro-propyl)-5-nitro-3H-benzoxazol-2-one was isolated as yellow solids (7.52 g, 99%). 1H-NMR (DMSO): 8.27 (d, 1H, J=2.2 Hz), 8.10 (dd, 1H, J=2.2, 8.8 Hz), 7.59 (d, 1H, J=8.8 Hz), 4.04 (t, 2H, J=6.7 Hz), 3.75 (t, 2H, J=6.5 Hz), 2.17 (m, 2H).

後処理

  1. temperatureThe reaction was cooled
  2. customThe layers were separated
  3. washwashed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered through a ½″h×2″w pad of SiO2 and conc. in vacuo
  6. customHexane, resulting in precipitation of the product
  7. customThe solids were triturated for 2 h
  8. filtrationcollected by filtration
  9. washwashed with hexane (2×60 mL)
  10. customAfter drying

出典と根拠

ORDレコード
ord-fbe5e794edd6475dae99cb71e23fcbd2
出典データセット
uspto-grants-2012_04
特許番号
US08148391B2

関連ノート

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