Cyanamide → HCID 15239022, compound

HRID 2395935Notes

Reaction equation

HRID 2395935 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 15239022HCID 15239022, compoundYield 51.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent2×

Conditions

Temperature
50 °C

Procedure

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 hydrochloricacid 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.

Workup

  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

Sources & evidence

ORD record
ord-e0eeff186010451f88fb08a71ea9d076
Source dataset
uspto-grants-1996_02
Patent number
US05491126

Reaction notes

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