Water → HCID 22612226, compound

HRID 844036Notes

Reaction equation

HRID 844036 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][C:6]1[N:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH2:10])=[O:9].[OH-].[K+].[CH2:20](Br)[CH:21]=[CH2:22].O>CS(C)=O>[CH2:22]([NH:10][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][CH:13]=[N:14][C:6]=1[O:5][C:4]1[CH:15]=[CH:16][CH:17]=[C:2]([Cl:1])[CH:3]=1)[CH:21]=[CH2:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 12114662-(3-chlorophenoxy)nicotinamide

Product 1

HCID 22612226HCID 22612226, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 2(3-chloro-phenoxy)-nicotinamide (0.084 g, 0.34 mmole) in methylsulfoxide (2 ml) was added potassium hydroxide powder (0.074 grams, 1.32 mmole) followed by allyl bromide ((0.082 grams, 0.68 mmole). After 1 hour the mixture was poured into water and extracted with methylene chloride. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give a clear film (0.011 g). 1H NMR (400 mhz, CD3OD) d 4.37 (q, J=7.26 Hz, 1H), 4.82 (d, J=5.60 Hz, 1H), 5.26 (d, J=10.58 Hz, 1H), 5.40 (d J=17.0 Hz, 1H), 6.05 (m, 1H), 7.03 (m, 1H), 7.13 (m, 1H), 7.21 (m, 2H), 7.38 (t J=8.1 Hz, 1H), 8.30 (m, 2H).

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organics were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a clear film (0.011 g)

Sources & evidence

ORD record
ord-7957c4d79c794a59b9039bf87c440926
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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