Cyanamide → HCID 15239022、化合物

HRID 274210ノート

反応式

HRID 274210 の反応式
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([N+:10]([O-:12])=O)[C:3]=1[NH2:4].[N:13]#[C:14][NH2:15]>C(O)(=O)C.Cl>[NH2:15][C:14]1[N:13]=[N+:10]([O-:12])[C:5]2[CH:6]=[C:7]([CH3:9])[CH:8]=[C:2]([Br:1])[C:3]=2[N:4]=1

参加物

5

反応物 2

HCID 9864CyanamideHCID 27753062-Bromo-4-methyl-6-nitroaniline

生成物 1

HCID 15239022HCID 15239022、化合物収率 51.5%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒2 回

反応条件

温度
50 °C

実験手順

To 13.0 g (56.3 mmol) of 2-bromo-4-methyl-6-nitroaniline stirring in a mixture of 25 ml glacial acetic acid and 5 ml of concentrated hydrochloric acid at 80° C., 29.0 g (690.5 mmol) of cyanamide and 25 ml of concentrated hydrochloric acid were added simultaneously, separately, and very slowly. At one point during the addition, a vigorous exotherm occurred and the external heat immediately removed. After the addition, the reaction was heated at reflux for 15 minutes. On cooling to about 50° C., 100 ml of 25% aqueous sodium hydroxide were added dropwise and the mixture heated at reflux 15 minutes. The reaction was cooled to room temperature, the insoluble orange solid filtered and washed with water followed by ethyl acetate to afford 7.4 g of yellow 3-amino-5-bromo-7-methyl-1,2,4-benzotriazine-1-oxide after drying.

後処理

  1. additionAt one point during the addition
  2. temperaturethe external heat immediately
  3. customremoved
  4. additionAfter the addition
  5. temperaturethe reaction was heated
  6. temperatureat reflux for 15 minutes
  7. addition100 ml of 25% aqueous sodium hydroxide were added dropwise
  8. temperaturethe mixture heated
  9. temperatureat reflux 15 minutes
  10. temperatureThe reaction was cooled to room temperature
  11. filtrationthe insoluble orange solid filtered
  12. washwashed with water

出典と根拠

ORDレコード
ord-c0c43d1f5a4140f0907303c196d1ba75
出典データセット
uspto-grants-1995_02
特許番号
US05389600

反応ノート

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