Sodium Nitrite → HCID 178518864、化合物

HRID 1723854

反応式

HRID 1723854 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1N.N([O-])=O.[Na+]>C(O)C.Cl.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:18])=[N:9]1

参加物

6

反応物 2

HCID 23668193Sodium NitriteHCID 685332472-amino-benzoic acid N'-(2-fluoro-phenyl)-hydrazide

生成物 1

HCID 178518864HCID 178518864、化合物収率 94%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
55 °C

実験手順

A stirred suspension of 105 g (0.429 mole) of 2-amino-benzoic acid N′-(2-fluoro-phenyl)-hydrazide in 1250 mL of ethanol and 1250 mL of 1N hydrochloric acid was heated to 55° C. A solution of 59 g (0.858 mole) of sodium nitrite in 200 mL of water was added dropwise over a 30 minute period. Approximately 10 minutes into the addition a solid began separating. External heating was continued until the reaction temperature reached 65° C. and then it was turned off. The temperature remained at 65-68° C. during the addition and gas evolution became vigorous approximately halfway through the addition. Toward the end of the addition, gas evolution slowed and the temperature dropped below 65° C. External heating was reapplied and the mixture was stirred at 70° C. for 3 hours. The mixture was cooled to −10° C. and filtered. The solid was rinsed once with 50 mL of ethanol, then once with 100 mL of water, and pressed dry under suction. Further drying in vacuo at 35° C. for 7 hours afforded 92 g (94%) of product.

後処理

  1. additionApproximately 10 minutes into the addition a solid
  2. custombegan separating
  3. temperatureExternal heating
  4. customreached 65° C.
  5. additionThe temperature remained at 65-68° C. during the addition and gas evolution
  6. additionthrough the addition
  7. additionToward the end of the addition, gas evolution
  8. additionthe temperature dropped below 65° C
  9. temperatureExternal heating
  10. temperatureThe mixture was cooled to −10° C.
  11. filtrationfiltered
  12. washThe solid was rinsed once with 50 mL of ethanol
  13. dry with materialonce with 100 mL of water, and pressed dry under suction
  14. customFurther drying in vacuo at 35° C. for 7 hours

出典と根拠

ORDレコード
ord-96f2362998ce4789b616c85e8fd21982
出典データセット
uspto-grants-2009_02
特許番号
US07485636B2

関連ノート

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