Ethylene Glycol → 2-(2-Hydroxyethoxymethyl)pyrazine

HRID 1605314Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1.[Na].[CH2:10]([OH:13])[CH2:11][OH:12]>>[OH:12][CH2:11][CH2:10][O:13][CH2:2][C:3]1[CH:8]=[N:7][CH:6]=[CH:5][N:4]=1

Participants

Reactant 3

HCID 174Ethylene Glycol

HCID 170169Pyrazine, 2-(chloromethyl)-

HCID 5360545Sodium

Product 1

HCID 205675442-(2-Hydroxyethoxymethyl)pyrazine

Procedure

2-Chloromethylpyrazine is reacted with the sodium salt of ethylene glycol to give 2-(2-hydroxyethoxymethyl)pyrazine which is treated with thionyl chloride to give 2-(2-chloroethoxymethyl)pyrazine. Using this intermediate in place of 4-(3-chloropropoxy)methylimidazole in the procedure of Example 22 gives the title compound.

Sources & evidence

ORD record: ord-38a476ac40db4fa1b183b08debab4e33
Source dataset: uspto-grants-1976_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03950333

Reaction notes

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