4-Hydroxybenzaldehyde → HCID 58043115、化合物

HRID 1035232ノート

反応式

HRID 1035232 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[CH:21]1[CH2:24][N:23]([C:25]([C:27]2[O:28][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[N:30][N:31]=2)=[O:26])[CH2:22]1)(=O)=O>CN(C=O)C>[C:32]1([C:29]2[O:28][C:27]([C:25]([N:23]3[CH2:24][CH:21]([O:1][C:2]4[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=4)[CH2:22]3)=[O:26])=[N:31][N:30]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

参加物

5

反応物 3

HCID 1264-HydroxybenzaldehydeHCID 10796Cesium carbonateHCID 580430991-(5-Phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate

生成物 1

HCID 58043115HCID 58043115、化合物収率 67.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

4-Hydroxybenzaldehyde (1.10 g, 9.17 mmol), cesium carbonate (3.49 g, 10.70 mmol) and 53B (2.70 g, 7.64 mmol) were mixed with DMF (80 mL). The mixture was stirred at 110° C. for 18 h and then cooled to RT. The solids were filtered off and the filtrate was evaporated. The residue was treated with methanol and the formed solid was collected by filtration. Drying under vacuum afforded 1.8 g (62%) of 68A as a beige solid. 1H NMR (500 MHz, DMSO-d6): δ 3.85 (s, 3H), 4.13 (dd, 1H), 4.57 (dd, 1H), 4.65 (dd, 1H), 5.12 (dd, 1H), 5.29 (m, 1H), 7.10 (d, 2H), 7.16 (d, 2H), 7.90 (d, 2H), 8.00 (d, 2H), 9.90 (s, 1H), MS (APCI+) m/z 380 [M+H]+.

後処理

  1. temperaturecooled to RT
  2. filtrationThe solids were filtered off
  3. customthe filtrate was evaporated
  4. additionThe residue was treated with methanol
  5. filtrationthe formed solid was collected by filtration
  6. customDrying under vacuum

出典と根拠

ORDレコード
ord-a6f001ddc15f4df7b2cdbc9caebaa8b0
出典データセット
uspto-grants-2013_10
特許番号
US08546375B2

反応ノート

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