O-Xylene → HCID 178507472, compound

HRID 722211Notes

Reaction equation

HRID 722211 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[Cl:10].C1(C)C(C)=CC=CC=1.C[Sn]([N:23]=[N+:24]=[N-:25])(C)C>CO>[Cl:10][C:3]1[CH:4]=[C:5]([C:6]2[NH:25][N:24]=[N:23][N:7]=2)[CH:8]=[CH:9][C:2]=1[NH2:1]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 5198964-Amino-3-chlorobenzonitrileHCID 5104973Azido(trimethyl)stannane

Product 1

HCID 178507472HCID 178507472, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
135 °C

Procedure

The mixture consisting of 1.07 g of 4-amino-3-chlorobenzonitrile, 30 ml of xylene and 1.7 g of trimethyltin azide was stirred at 135° C. for 8 hours. After cooling, 25 ml of methanol were added, the mixture was stirred at room temperature for 30 minutes and the volatile constituents were removed on a rotary evaporator. On stirring, a solid precipitated out of the mixture obtained in this way, and was filtered off with suction and briefly dried under reduced pressure. This solid was dissolved in 1N sodium hydroxide solution and filtered, and the product was precipitated by acidifying with 2N hydrochloric acid, filtered off with suction and dried under reduced pressure.

Workup

  1. temperatureAfter cooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. customthe volatile constituents were removed on a rotary evaporator
  4. stirringOn stirring
  5. customa solid precipitated out of the mixture
  6. customobtained in this way
  7. filtrationwas filtered off with suction
  8. custombriefly dried under reduced pressure
  9. dissolutionThis solid was dissolved in 1N sodium hydroxide solution
  10. filtrationfiltered
  11. customthe product was precipitated
  12. filtrationfiltered off with suction
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-6175afaac9d54f92ae43f443a1909ca0
Source dataset
uspto-grants-2006_11
Patent number
US07138414B2

Reaction notes

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