2-(2-Amino-1,3-thiazol-4-yl)acetamide → 4-Thiazoleacetonitrile, 2-amino-

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

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

customThe mixture was evaporated under reduced pressure
additionpoured onto a mixture of ice water and ethyl acetate
extractionextracted repeatedly with ethyl acetate
extractionThe combined extract
dry with materialwas dried (MgSO4)
customevaporated
customThe residue was purified by chromatography
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-d0ad4b5a45564d7898a3883e7bdd7a32
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06107297

Reaction notes

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Participants

Reactant 1

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

Product 1

HCID 186897514-Thiazoleacetonitrile, 2-amino-

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent