1,4-Dioxane → HCID 86610487, compound

HRID 2416184Notes

Reaction equation

HRID 2416184 reaction equation
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.ClCC(=O)[CH2:13][C:14]([O:16][CH3:17])=[O:15].O1CCO[CH2:21][CH2:20]1>>[CH3:17][O:16][C:14](=[O:15])[CH2:13][C:1]1([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[NH:9][CH:21]=[CH:20][S:8]1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 36240Methyl 4-chloroacetoacetateHCID 27237884-Pyridinecarbothioamide

Product 1

HCID 86610487HCID 86610487, compound

Conditions

Temperature
75 °C

Procedure

In an oven-dried, 100-mL, round-bottomed flask was placed thioisonicotinamide (Pflaltz-Bauer) (2.9 g, 21 mmol) in 1,4-dioxane (60 mL). Methyl 4-chloroacetoacetate (Aldrich, 3.16 g, 2.4 mL, 21 mmol) was added at RT. The flask was purged with N2 and the solution was heated to 75° C. for 12 h. The mixture was cooled to RT, quenched with 2N NH3 in MeOH (10 mL), and concentrated. The material was purified by flash chromatography on silica gel (EtOAc/hexane, 50:50) to afford 2-(4-pyridyl)-thiazole acetic acid methyl ester as a light yellow solid. Mp: 78-79° C. MS m/z: 235 (M+1). Calc'd for C11H10N2O2S: 234.05.

Workup

  1. customThe flask was purged with N2
  2. temperatureThe mixture was cooled to RT
  3. customquenched with 2N NH3 in MeOH (10 mL)
  4. concentrationconcentrated
  5. customThe material was purified by flash chromatography on silica gel (EtOAc/hexane, 50:50)

Sources & evidence

ORD record
ord-e396df50f8af41718e9dc3d6925c46c5
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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