Ethyl Nitrite → Thiazole, 5-(methoxymethyl)-4-methyl-

HRID 2071922Notes

Reaction equation

HRID 2071922 reaction equation
N[C:2]1[S:3][C:4]([CH2:8][O:9][CH3:10])=[C:5]([CH3:7])[N:6]=1.C(ON=O)C>O1CCCC1>[CH3:10][O:9][CH2:8][C:4]1[S:3][CH:2]=[N:6][C:5]=1[CH3:7]

Participants

4

Reactant 2

HCID 8026Ethyl NitriteHCID 127781692-Amino-5-methoxymethyl-4-methylthiazole

Product 1

HCID 11571819Thiazole, 5-(methoxymethyl)-4-methyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3.2 g. of 2-amino-5-methoxymethyl-4-methylthiazole in 100 ml. of dry tetrahydrofuran was brought to reflux and a solution of 6 g. of ethylnitrite in 75 ml. of dry tetrahydrofuran was added dropwise to the refluxing solution. After refluxing an additional 5 hours, the mixture was cooled and evaporated to give an oil. The oil was extracted into hexane and the hexane solution was evaporated to dryness to give 5-methoxymethyl-4-methylthiazole.

Workup

  1. temperatureto reflux
  2. temperatureAfter refluxing an additional 5 hours
  3. temperaturethe mixture was cooled
  4. customevaporated
  5. customto give an oil
  6. extractionThe oil was extracted into hexane
  7. customthe hexane solution was evaporated to dryness

Sources & evidence

ORD record
ord-cfa306b9475844aa863a39231953909d
Source dataset
uspto-grants-1977_09
Patent number
US04049669

Reaction notes

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