Hydrochloric Acid → HCID 178518972、化合物

HRID 260891ノート

反応式

HRID 260891 の反応式
[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

参加物

8

反応物 5

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

生成物 1

HCID 178518972HCID 178518972、化合物収率 92%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-67673b7c25174711abc135355d590cc3
出典データセット
uspto-grants-1996_06
特許番号
US05530135

反応ノート

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