Ethanol → 6,7-Dichloro-3,4-dihydro-4-methyl-2H-pyrazino(2,3-b)(1,4)oxazine

HRID 437025Notes

Reaction equation

HRID 437025 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[N:4][C:3]=1Cl.[CH3:11][NH:12][CH:13](O)[CH3:14].[Na].C([OH:19])C>>[Cl:9][C:5]1[C:6]([Cl:8])=[N:7][C:2]2[O:19][CH2:14][CH2:13][N:12]([CH3:11])[C:3]=2[N:4]=1

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 311820TetrachloropyrazineHCID 5247031N-MethylaminoethanolHCID 5360545Sodium

Product 1

HCID 214299406,7-Dichloro-3,4-dihydro-4-methyl-2H-pyrazino(2,3-b)(1,4)oxazineYield 27%

Procedure

The crude product from the reaction of tetrachloropyrazine (10.8 g, 0.05 mol) and methylaminoethanol (3.7 g, 0.05 mol) in Example 1 above was dissolved in absolute ethanol and small pieces of sodium (1.2 g, 0.05 mol) were added. After stirring overnight the ethanol was evaporated and the solid residue was washed with water, filtered, and dried on a porous plate to a weight of 7 g. The solid was recrystallized from ethanol and isopropyl alcohol (IPA) to give 4 g (27% yield) of a white solid, m.p. 170°-2°.

Workup

  1. customwas evaporated
  2. washthe solid residue was washed with water
  3. filtrationfiltered
  4. customdried on a porous plate to a weight of 7 g
  5. customThe solid was recrystallized from ethanol and isopropyl alcohol (IPA)

Sources & evidence

ORD record
ord-fd649fd78f304026961c408ab3146e30
Source dataset
uspto-grants-1977_06
Patent number
US04029657

Reaction notes

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