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

HRID 515211노트

반응식

HRID 515211 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
125 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c7c223fec1564661bd299b6f57028ed1
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108937B2

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