Sulfuric Acid → 5-Trifluoromethylbenzofuroxan

HRID 66958

反応式

HRID 66958 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=O.S(=O)(=O)(O)[OH:16].N([O-])=O.[Na+].NC(N)=O.[N-]=[N+]=[N-].[Na+]>C1(C)C=CC=CC=1.O.C(O)(=O)C>[CH:6]1[C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]2[C:2](=[N+:1]([O-:16])[O:14][N:12]=2)[CH:7]=1

参加物

9

反応物 5

HCID 1118Sulfuric AcidHCID 1176UreaHCID 33557Sodium AzideHCID 67865Benzenamine, 2-nitro-4-(trifluoromethyl)-HCID 23668193Sodium Nitrite

生成物 1

HCID 102623155-Trifluoromethylbenzofuroxan

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 1140Toluene溶媒2 回

実験手順

A solution of 103 grams (0.5 mole) of 4-amino-3-nitro-benzotrifluoride, 750 ml. of acetic acid and 385 ml. of concentrated sulfuric acid is cooled in an ice-bath with sufficient stirring. Sodium nitrite (38 grams, 0.55 moles) is added portionwise at such a rate that the reaction temperature does not exceed 5° C. After addition is complete, 38 grams of urea is added, and with vigoroug stirring 32.5 grams of sodium azide is then added. Stirring is continued for 20 minutes, then the reaction mixture is poured into 4 liters of ice and water. The crude product, 4-azido-3-nitrobenzotrifluoride is extracted from the aqueous mixture with chloroform. The extract is dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to furnish an oily-residue which is taken up in 800 ml. of toluene. The toluene solution is heated under reflux for 18 hours behind a shatter-proof shield. After cooling to room temperature, the solvent is evaporated and the residue is distilled under reduced pressure. The fraction boiling at 105°-108° C. (16 ml.) is considered to be sufficiently pure 5-trifluoromethylbenzofuroxan; yield, 62.3 (60 percent).

後処理

  1. customdoes not exceed 5° C
  2. additionAfter addition
  3. additionis then added
  4. extractionThe crude product, 4-azido-3-nitrobenzotrifluoride is extracted from the aqueous mixture with chloroform
  5. dry with materialThe extract is dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto furnish an oily-residue which
  9. temperatureunder reflux for 18 hours behind a shatter-proof shield
  10. customthe solvent is evaporated
  11. distillationthe residue is distilled under reduced pressure
  12. customyield

出典と根拠

ORDレコード
ord-d3f3645100c54ccf9f2073273a55f333
出典データセット
uspto-grants-1982_08
特許番号
US04343942

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