Iodoethane → HCID 67273887, compound

HRID 601443Notes

Reaction equation

HRID 601443 reaction equation
[OH-].[K+].[C:3]([C:6]1[S:10][C:9](=[O:11])[NH:8][C:7]=1[CH3:12])(=[O:5])[CH3:4].I[CH2:14][CH3:15]>CS(C)=O>[C:3]([C:6]1[S:10][C:9](=[O:11])[N:8]([CH2:14][CH3:15])[C:7]=1[CH3:12])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 21793266HCID 21793266, compound

Product 1

HCID 67273887HCID 67273887, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

KOH (1.476 g, 26.31 mmol) was added to a solution of 5-acetyl-4-methyl-3H-thiazol-2-one (4.134 g, 26.31 mmol) in DMSO (10 mL), and stirred at room temperature for 30 min. Iodoethane (2.525 mL, 31.57 mmol) was added and the resulting mixture stirred for 72 h. The reaction mixture was extracted into CH2Cl2 (5×30 mL) from H2O (30 mL) and the combined organic layers were dried over MgSO4, before passing through a short SiO2 gel column. Pooling of the desired fractions yielded the title compound (3.104 g, 64%).

Workup

  1. stirringthe resulting mixture stirred for 72 h
  2. extractionThe reaction mixture was extracted into CH2Cl2 (5×30 mL) from H2O (30 mL)
  3. dry with materialthe combined organic layers were dried over MgSO4

Sources & evidence

ORD record
ord-ec1b3ab81f2745e09e7def63d7ab2034
Source dataset
uspto-grants-2011_03
Patent number
US07902361B2

Reaction notes

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