Hydrochloric Acid → 6-Bromo-1-methyl-1,3-dihydrobenzo[c][1,2,5]thiadiazole 2,2-dioxide

HRID 515211ノート

反応式

HRID 515211 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][CH3:10])[C:5]([NH2:8])=[CH:6][CH:7]=1.[S:11](N)(N)(=[O:13])=[O:12].N1C=CC=CC=1.Cl>C(OCC)(=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][S:11](=[O:13])(=[O:12])[N:9]([CH3:10])[C:4]=2[CH:3]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 82267SulfamideHCID 121982705-Bromo-N1-methylbenzene-1,2-diamine

生成物 1

HCID 674127626-Bromo-1-methyl-1,3-dihydrobenzo[c][1,2,5]thiadiazole 2,2-dioxide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
125 °C

実験手順

To a round bottom flask was added 4-bromo-N2-methylbenzene-1,2-diamine (1-2) (9.07 g, 45.1 mmol), sulfamide (8.84 g, 92 mmol), and finally anhydrous pyridine (75 mL). The reaction mixture was then heated to 125° C. while stirring in a hot oil bath with a water cooled reflux condenser attached under an atmosphere of nitrogen for 14 hours. The crude reaction mixture was then allowed to cool to room temperature, suspended in ethyl acetate and added 6N HCl until pH <3. Crude mixture was then filtered. Filtrate organics were separated, then washed with 6N HCl twice dried over sodium sulfate, filtered, and concentrated to give 6-bromo-1-methyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (1-3). HRMS (M+H)+: observed=262.9486, calculated=262.9484.

後処理

  1. temperaturecooled
  2. temperaturereflux condenser
  3. customThe crude reaction mixture
  4. temperatureto cool to room temperature
  5. filtrationCrude mixture was then filtered
  6. customFiltrate organics were separated
  7. washwashed with 6N HCl
  8. dry with materialtwice dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-c7c223fec1564661bd299b6f57028ed1
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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