Hydrochloric Acid → HCID 178518972, 화합물

HRID 260891노트

반응식

HRID 260891 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]=[C:17]=[O:18].N([O-])=O.[Na+].Cl>O.CN(C)C=O>[CH:13]1[CH:12]=[C:11]([N:16]2[NH:7][N:6]=[N:5][C:17]2=[O:18])[C:10]([Cl:9])=[CH:15][CH:14]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 76833Chlorophenyl isocyanateHCID 6451240Aluminum(III) ChlorideHCID 23668193Sodium Nitrite

생성물 1

HCID 178518972HCID 178518972, 화합물수율 92%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Anhydrous aluminum chloride (1.5 g) was added to N,N-dimethylformamide (20 ml) under ice cooling and the resulting mixture was stirred for fifteen minutes. To the mixture was added sodium azide (0.65 g), followed by a 15 minute-stirring, addition of 2-chlorophenylisocyanate (1.53 g) and heating at 70° to 75° C. for three hours, in that order. After cooling, the reaction mixture was added with stirring to a mixture of sodium nitrite (1 g), water (200 ml) and ice (100 g) and the resulting mixture was acidified was 10% hydrochloric acid (until a potassium iodide starch paper became discolored), followed by extraction with ethyl acetate. The thus obtained ethyl acetate layer was washed with water, dried over sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by flash column chromatography (eluent: hexane:ethyl acetate = 2:1) to obtain the desired 1-(2-chlorophenyl)-5(4H)-tetrazolinone (1.8 g) having a m.p. in the range of from 124.5° C. to 125.5° C. in a yield of 92% of theory.

후처리

  1. stirring-stirring
  2. temperatureheating at 70° to 75° C. for three hours, in that order
  3. temperatureAfter cooling
  4. additionthe reaction mixture was added
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe thus obtained ethyl acetate layer was washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated under reduced pressure
  9. customThe resulting residue was purified by flash column chromatography (eluent: hexane:ethyl acetate = 2:1)

출처 및 근거

ORD 기록
ord-67673b7c25174711abc135355d590cc3
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05530135

반응 노트

불러오는 중…