Nitrite → Propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amine

HRID 1942335노트

반응식

HRID 1942335 반응식
Br.Br.[CH2:3]([NH:6][CH:7]1[CH2:16][CH2:15][C:10]2[N:11]=[C:12](N)[S:13][C:9]=2[CH2:8]1)[CH2:4][CH3:5].N([O-])=O.P(P(O)(O)=O)(O)(O)=O.[OH-].[Na+]>Cl>[CH2:3]([NH:6][CH:7]1[CH2:16][CH2:15][C:10]2[N:11]=[CH:12][S:13][C:9]=2[CH2:8]1)[CH2:4][CH3:5]

참가 물질

6

반응물 4

HCID 946NitriteHCID 14798Sodium HydroxideHCID 24536Hypophosphoric acidHCID 86651296N6-propyl-4,5,6,7-tetrahydro-benzothiazole-2,6-diamine dihydrobromide

생성물 1

HCID 18705889Propyl-(4,5,6,7-tetrahydro-benzothiazol-6-yl)-amine

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

반응 조건

온도
-30 °C

실험 절차

To a solution of 14.5 g (38.9 mmol) N6-propyl-4,5,6,7-tetrahydro-benzothiazole-2,6-diamine dihydrobromide in 220 mL concentrated aqueous hydrochloric acid at −30° C. is drop wise added 66.3 mL of an aqueous 1N solution nitrite over the course of 30 minutes. After further stirring for 1 hour at the same temperature 5.44 ml (52.5 mmol) of a 50% aqueous solution hypophosphoric acid is added. The reaction mixture is stored at 4° C. overnight. After having cooled down the solution again to −30° C. the mixture is slowly basified with 40% aqueous sodium hydroxide solution while temperature is kept at −30° C. The resulting mixture is warmed up to room temperature and extracted with Chloroform/Ethanol 5:1 (3×250 mL) The solution is dried over anhydrous sodium sulfate and concentrated in vacuum. The brown oil obtained is chromatographed over silica gel, eluting with dichloromethane/methanol 97:3 under ammonia atmosphere.

후처리

  1. customat −30° C.
  2. customover the course of 30 minutes
  3. additionis added
  4. customis kept at −30° C
  5. temperatureThe resulting mixture is warmed up to room temperature
  6. extractionextracted with Chloroform/Ethanol 5:1 (3×250 mL) The solution
  7. dry with materialis dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuum
  9. customThe brown oil obtained
  10. customis chromatographed over silica gel
  11. washeluting with dichloromethane/methanol 97:3 under ammonia atmosphere

출처 및 근거

ORD 기록
ord-a5d414f148fb479688f7c99dfe283d04
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389555B2

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