2-(2-amino-1,3-thiazol-4-yl)acetamide → HCID 18689751, compound

HRID 1872011Notes

Reaction equation

HRID 1872011 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH2:10])=O)[N:6]=1>P(Cl)(Cl)(Cl)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]#[N:10])[N:6]=1

Participants

3

Reactant 1

HCID 70640912-(2-amino-1,3-thiazol-4-yl)acetamide

Product 1

HCID 18689751HCID 18689751, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the product from step (i) (9.5 g) and phosphorous oxychloride (30 ml) was heated at 90° C. for 2 hours. The mixture was evaporated under reduced pressure and poured onto a mixture of ice water and ethyl acetate. The aqueous phase was adjusted to pH 9 with sodium bicarbonate and extracted repeatedly with ethyl acetate. The combined extract was dried (MgSO4) and evaporated. The residue was purified by chromatography eluting with ethyl acetate. Yield 6.1 g. 1H NMR: δ (DMSO) 7.08(br s,2H), 6.40(s,1H), 3.77(s,2H).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. additionpoured onto a mixture of ice water and ethyl acetate
  3. extractionextracted repeatedly with ethyl acetate
  4. extractionThe combined extract
  5. dry with materialwas dried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-d0ad4b5a45564d7898a3883e7bdd7a32
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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