Ethanol → HCID 86606419, compound

HRID 2218526Notes

Reaction equation

HRID 2218526 reaction equation
[Na].Cl[CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10](=[O:12])[CH3:11])[S:7][CH:8]=1.[CH2:13]([OH:15])[CH3:14]>>[CH2:13]([O:15][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10](=[O:12])[CH3:11])[S:7][CH:8]=1)[CH3:14]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 819632-Acetamido-4-chloromethylthiazoleHCID 5360545Sodium

Product 1

HCID 86606419HCID 86606419, compoundYield 42%

Procedure

The sodium metal (16 mg, 0.681 mmol) was dissolved in 2 ml of anhydrous ethanol. To this solution was added a suspension of N-(4-(chloromethyl)thiazol-2-yl)acetamide (100 mg, 0.521 mmol) in ethanol (1 ml). The reaction was stirred at room temperature for 1 hour and then heated at 63° C. for 1 hour. The reaction was concentrated and the residue was purified via preparative HPLC to afford N-(4-ethoxymethyl-thiazol-2-yl)-acetamide as a yellow amorphous solid (44 mg, 42%). LC/MS m/z 199.16 (M-1)+; HPLC Rt: 1.79 min.

Workup

  1. additionTo this solution was added
  2. temperatureheated at 63° C. for 1 hour
  3. concentrationThe reaction was concentrated
  4. customthe residue was purified via preparative HPLC

Sources & evidence

ORD record
ord-b72db1adf0e64a5ba8173591047e3712
Source dataset
uspto-grants-2008_08
Patent number
US07411071B2

Reaction notes

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