Cesium carbonate → 5-Bromo-1-(cyclopropylmethyl)-3-methyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

HRID 515212ノート

反応式

HRID 515212 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][S:8](=[O:11])(=[O:10])[N:7]([CH3:12])[C:6]=2[CH:13]=1.CN1[C:19](=O)[CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[Cs+].[Cs+].BrCC1CC1>C(OCC)(=O)C.O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([CH2:16][CH:17]3[CH2:19][CH2:18]3)[S:8](=[O:11])(=[O:10])[N:7]([CH3:12])[C:6]=2[CH:13]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 81503BromomethylcyclopropaneHCID 674127626-Bromo-1-methyl-1,3-dihydrobenzo[c][1,2,5]thiadiazole 2,2-dioxide

生成物 1

HCID 674107445-Bromo-1-(cyclopropylmethyl)-3-methyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a round bottom flask was added 6-bromo-1-methyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (1-3) (5.32 g, 20.2 mmol), anhydrous NMP (10 mL), anhydrous 1,4 Dioxane (100 mL), cesium carbonate (13.2 g, 40.4 mmol), followed by (bromomethyl)cyclopropane (3.00 g, 22.2 mmol). The reaction mixture was then heated to 100° C. while stirring in a hot oil bath for 18 hours. The crude reaction mixture was then cooled to room temperature, then suspended in ethyl acetate and washed with a saturated solution of sodium bicarbonate, followed by water, then brine, dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel chromatography (0-40% EtOAc/Hex) to give 5-bromo-1-(cyclopropylmethyl)-3-methyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (1-4) as a tan solid. HRMS (M+H)+: observed=316.9953, calculated=316.9954.

後処理

  1. customThe crude reaction mixture
  2. temperaturewas then cooled to room temperature
  3. washwashed with a saturated solution of sodium bicarbonate
  4. dry with materialbrine, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel chromatography (0-40% EtOAc/Hex)

出典と根拠

ORDレコード
ord-fa054024c3644edc99f2ed9975e7506f
出典データセット
uspto-grants-2015_08
特許番号
US09108937B2

反応ノート

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