Ammonia → 2,6-DIAMINO-3-(2,3,5-TRICHLOROPHENYL)-PYRAZINE

HRID 1383309Notes

Reaction equation

HRID 1383309 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]([Cl:15])[C:9]=2[Cl:16])=[N:6][CH:5]=[C:4](Cl)[N:3]=1.[NH3:18]>C(O)C>[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[C:10]([Cl:15])[C:9]=2[Cl:16])=[N:6][CH:5]=[C:4]([NH2:18])[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10990505HCID 10990505, compound

Product 1

HCID 99260012,6-DIAMINO-3-(2,3,5-TRICHLOROPHENYL)-PYRAZINE

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
180 °C

Procedure

A suspension of 2-amino-6-chloro-3-(2,3,5-trichlorophenyl)pyrazine (0.3 g, 9.71×10−4 mole) in absolute ethanol (4 ml) and 0.880 aqueous ammonia (8.24 ml) was stirred and heated in an autoclave at 180° C. for 44 hrs. The cooled mixture was evaporated in vacuo, and the residue extracted with chloroform (3×30 ml). The combined chloroform extracts were dried over anhydrous magnesium sulphate, filtered and the filtrate evaporated down in vacuo. The residue was purified by ‘flash chromatography’ using chloroform to 98:2 chloroform:methanol as the eluent. The product was triturated with 40-60° C. petroleum ether, filtered and dried in vacuo. Yield 0.155 g (56%), M.p. 178-180° C.

Workup

  1. customThe cooled mixture was evaporated in vacuo
  2. extractionthe residue extracted with chloroform (3×30 ml)
  3. dry with materialThe combined chloroform extracts were dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customthe filtrate evaporated down in vacuo
  6. customThe residue was purified by ‘flash chromatography’
  7. customThe product was triturated with 40-60° C. petroleum ether
  8. filtrationfiltered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-b7f24e7b92694ceaa4332ae4bc98cdcc
Source dataset
uspto-grants-2001_07
Patent number
US06255307B1

Reaction notes

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