Methanol → HCID 12044217, compound

HRID 2094801Notes

Reaction equation

HRID 2094801 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[CH2:10])=[N:7][CH:8]=1)[CH3:2].BrN1C(=[O:17])CCC1=O.C([O-])([O-])=O.[K+].[K+].CO>CS(C)=O.O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:10][O:17]2)=[N:7][CH:8]=1)[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 222462Pyridine, 5-ethyl-2-vinyl-2×

Product 1

HCID 12044217HCID 12044217, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 400 g (2.974 mol) 5-ethyl-2-vinyl-pyridine dissolved in a mixture of 1000 mL of dimethyl sulfoxide and 106 mL water, was added 741.9 g (4.16 mol) N-bromosuccinimide at 0 to −5° C. Reaction mixture was stirred for 1 hr. The progress of reaction was monitored by TLC and after complete consumption of 5-ethyl-2-vinyl-pyridine, 833 g (6.015 mol) of K2CO3 along with 400 mL methanol was added at 25-30° C. Stirring was continued for 1 hr. and after subsequent work-up 358.49 g (80%) of the desired product was obtained.

Workup

  1. customReaction mixture
  2. customThe progress of reaction
  3. additionwas added at 25-30° C
  4. stirringStirring
  5. waitwas continued for 1 hr

Sources & evidence

ORD record
ord-e6395f466bca47ef85c42791169b1df0
Source dataset
uspto-grants-2013_05
Patent number
US08445685B2

Reaction notes

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