2-Amino-4-methylthiazole → HCID 44313067, compound

HRID 1252155Notes

Reaction equation

HRID 1252155 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:6][CH:7]=O)[CH2:3][CH:4]=O.[NH2:10][C:11]1[S:12][CH:13]=[C:14]([CH3:16])[N:15]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:9])[CH:6]=[CH:7][N:10]([C:11]2[S:12][CH:13]=[C:14]([CH3:16])[N:15]=2)[CH:4]=[CH:3]1

Participants

5

Reactant 3

HCID 741432-Amino-4-methylthiazoleHCID 521998p-Toluenesulfonic acid monohydrateHCID 11116082HCID 11116082, compound

Product 1

HCID 44313067HCID 44313067, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 170 ml of benzene, 4.45 l g (0.035 mole) of 3,3-dimethylglutaraldehyde was combined with 3.96 (0.035 mole) of 2-amino-4-methylthiazole under nitrogen. The reaction mixture was brought to reflux and water azeotroped off via a Dean-Stark trap. After 21 hours 0.20 g (0.001 mole) of p-toluenesulfonic acid monohydrate was added to the reaction mixture and heating continued an additional 5 hours after which the solvent was evaporated in vacuo. The crude product was purified by silica gel flash chromatography eluting with a 1% ethyl acetate/hexane solution. The eluate was evaporated in vacuo to yield 2.67 g of the title compound as a clear liquid.

Workup

  1. temperatureto reflux
  2. customwater azeotroped off via a Dean-Stark trap
  3. temperatureheating
  4. customafter which the solvent was evaporated in vacuo
  5. customThe crude product was purified by silica gel flash chromatography
  6. washeluting with a 1% ethyl acetate/hexane solution
  7. customThe eluate was evaporated in vacuo

Sources & evidence

ORD record
ord-a24052bfa0d9458dacd422d09761998e
Source dataset
uspto-grants-1988_05
Patent number
US04742068

Reaction notes

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