Triethylamine → 3-(4-chloro-3-nitrobenzylidene)-3H-isobenzofuran-1-one

HRID 459775

반응식

HRID 459775 반응식
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4](P(=O)(OC)OC)[O:3]1.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][C:19]=1[N+:26]([O-:28])=[O:27].C(N(CC)CC)C>O1CCCC1>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2](=[O:1])[O:3]2)=[CH:20][C:19]=1[N+:26]([O-:28])=[O:27]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 855054-Chloro-3-nitrobenzaldehydeHCID 11118213Dimethyl (3-oxo-1,3-dihydro-2-benzofuran-1-yl)phosphonate

생성물 1

HCID 686228163-(4-chloro-3-nitrobenzylidene)-3H-isobenzofuran-1-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
15 °C

실험 절차

A stirred solution of dimethyl 3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonate (4.84 g, 0.02 mol; prepared in a manner similar to that described in Example 23) and 4-chloro-3-nitrobenzaldehyde (3.71 g, 0.02 mol) in tetrahydrofuran (30 ml) was cooled to 15° C. and a solution of triethylamine (2.02 g, 0.02 mol) in tetrahydrofuran (3 ml) was added dropwise at <25° C. The mixture was stirred at ambient temperature for 1 hour, allowed to stand at this temperature for a further 16 hours and the resulting solid was collected by filtration. The filtrate was concentrated in vacuo, the residue was triturated with water (5 ml) and the resulting solid was collected by filtration. The two crops of solid were combined and suspended in water (30 ml). The mixture was stirred at ambient temperature for 30 minutes and the resulting solid was collected by filtration and dried in vacuo for 24 hours to give crude 3-(4-chloro-3-nitrobenzylidene)-3H-isobenzofuran-1-one as a pale yellow solid, m.pt. 198–204° C., still slightly wet with water, which was used directly in the next stage.

후처리

  1. customprepared in a manner similar to
  2. waitto stand at this temperature for a further 16 hours
  3. filtrationthe resulting solid was collected by filtration
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was triturated with water (5 ml)
  6. filtrationthe resulting solid was collected by filtration
  7. stirringThe mixture was stirred at ambient temperature for 30 minutes
  8. filtrationthe resulting solid was collected by filtration
  9. customdried in vacuo for 24 hours

출처 및 근거

ORD 기록
ord-eef7148da5474d7cb8dcb63a22b909da
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196085B2

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