Ethanol → HCID 67263489、化合物

HRID 1041665ノート

反応式

HRID 1041665 の反応式
[OH-].[K+].Cl[CH2:4][CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=2[O:9][C:8]1=[O:19].[CH2:20]([OH:22])[CH3:21]>>[CH2:20]([O:22][C:8]([N:7]1[C:11]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=2[O:9][CH2:4][CH2:5][CH2:6]1)=[O:19])[CH3:21]

参加物

4

反応物 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 434479093-(3-Chloropropyl)-5-nitrobenzo[d]oxazol-2(3H)-one

生成物 1

HCID 67263489HCID 67263489、化合物収率 77%

反応条件

温度
80 °C

実験手順

Potassium hydroxide (2.19 g, 33.2 mmol) was dissolved in Ethanol (150 mL) and 3-(3-Chloro-propyl)-5-nitro-3H-benzoxazol-2-one (8.11 g, 31.6 mmol) was added. After 2 h, the mixture was concentrated in vacuo, and the solids redissolved in N,N-Dimethylformamide (150 mL). The mixture was heated to 80° C. for 2 h. The mixture was cooled and diluted with 500 mL EtOAc and washed with water (4×50 mL). The aq. washes were back extracted with 100 mL EtOAc. The combined organics were washed with water (50 mL) and brine (100 mL), dried over sodium sulfate and conc. in vacuo to give orange solids, which were triturated in 10% Ether:Hexane (100 mL) overnight. The orange solids were collected and washed with hexane to furnish 2-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocycloheptene-9-carboxylic acid ethyl ester (6.45 g, 77%). 1H-NMR (DMSO): 8.19 (s, 1H), 8.02 (d, 1H, J=8.9 Hz), 7.19 (d, 1H, J=8.9 Hz), 4.25 (m, 2H), 4.15 (m, 2H), 3.76 (m, 2H), 2.05 (m, 2H), 1.19 (m, 3H).

後処理

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionthe solids redissolved in N,N-Dimethylformamide (150 mL)
  3. temperatureThe mixture was cooled
  4. additiondiluted with 500 mL EtOAc
  5. washwashed with water (4×50 mL)
  6. extractionThe aq. washes were back extracted with 100 mL EtOAc
  7. washThe combined organics were washed with water (50 mL) and brine (100 mL)
  8. dry with materialdried over sodium sulfate and conc. in vacuo
  9. customto give orange solids, which
  10. customwere triturated in 10% Ether
  11. customHexane (100 mL) overnight
  12. customThe orange solids were collected
  13. washwashed with hexane

出典と根拠

ORDレコード
ord-b6e19d0b3d0e4fb58a6727be3949b084
出典データセット
uspto-grants-2013_10
特許番号
US08552186B2

反応ノート

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