Ethanolamine → Ethanol, 2-((6-amino-3-chloro-5-nitropyrazinyl)amino)-

HRID 1649533Notes

Reaction equation

HRID 1649533 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([NH2:9])=[N:6][C:7]=1Cl.C(N(CC)CC)C.[NH2:20][CH2:21][CH2:22][OH:23]>C(O)(C)C>[NH2:9][C:5]1[N:6]=[C:7]([NH:20][CH2:21][CH2:22][OH:23])[C:2]([Cl:1])=[N:3][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 130629765,6-Dichloro-3-nitropyrazin-2-amine

Product 1

HCID 174576Ethanol, 2-((6-amino-3-chloro-5-nitropyrazinyl)amino)-

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 1.0 g of 5,6-dichloro-3-nitropyrazinamine in 20 ml isopropanol is added 0.5 ml triethylamine and then 0.3 ml 2-aminoethanol. The reaction mixture is stirred for 3 hours and then concentrated in vacuo to solids. The solids are triturated with hot chloroform and recrystallized from acetonitrile to afford 0.6 g of 2[(6-Amino-3-chloro-5-nitropyrazin-2-yl)amino]ethanol, m.p. 196°-197° C.

Workup

  1. concentrationconcentrated in vacuo to solids
  2. customThe solids are triturated with hot chloroform
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-862984bc49bf4584a0247fcbe4308116
Source dataset
uspto-grants-1983_11
Patent number
US04418062

Reaction notes

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