Triethylamine → 3-[(3-Nitro-2-pyrazinyl)amino]-1,2-propanediol

HRID 247572

Reaction equation

HRID 247572 reaction equation
Cl[C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.C(N(CC)CC)C.[NH2:18][CH2:19][CH:20]([OH:23])[CH2:21][OH:22]>C(O)(C)C>[OH:23][CH:20]([CH2:21][OH:22])[CH2:19][NH:18][C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 735613-Amino-1,2-propanediolHCID 159142352-Chloro-3-nitropyrazine

Product 1

HCID 159142393-[(3-Nitro-2-pyrazinyl)amino]-1,2-propanediol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 1.5 g (0.0094 mol) 3 and 1.01 g (0.01 mol) triethylamine in 25 ml isopropanol is added 0.91 g (0.01 mol) 3-amino-1,2-propanediol (10). The reaction mixture becomes reddish and is stirred at room temperature for 16 hours. The solvent is then removed on the rotary evaporator and the residue is purified by flash chromatography on silica gel to afford pure 11 as a yellow solid, m.p. 100°-102°.

Workup

  1. customThe solvent is then removed on the rotary evaporator
  2. customthe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-19875c21720f4be89ee79571b65fe5c4
Source dataset
uspto-grants-1987_11
Patent number
US04709035

Linked notes

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