1-Bromononane → HCID 21187959, compound

HRID 1584904Notes

Reaction equation

HRID 1584904 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:20])[C:7]=1[NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([OH:18])[CH:11]=1.[H-].[Na+].Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>CN(C)C=O.O>[Cl:20][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:11]=1

Participants

6

Reactant 3

HCID 127421-BromononaneHCID 24758Sodium hydrideHCID 18366000HCID 18366000, compound

Product 1

HCID 21187959HCID 21187959, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of N-(3,5-dichloropyrid-4-yl)-3-hydroxy-4-methoxybenzamide (2.0 g; that is prepared as described in Reference Example 12) in dimethylformamide (20 mL) at room temperature under nitrogen is treated portionwise with a suspension of sodium hydride (60% dispersion in oil; 0.26 g), and then it is stirred for a further hour at room temperature. It is then treated dropwise with 1-bromononane (1.2 mL) and stirred at 60° C. for 5 hours. The solution is then cooled to room temperature, diluted with water (60 mL), and extracted with ethyl acetate (2×100 mL). The combined organic extracts are dried over magnesium sulfate and evaporated, to give a white solid, which is subjected to flash chromatography on silica gel, eluting with t-butyl methyl ether, to give N-(3,5-dichloropyrid-4-yl)-3-nonyloxy-4-methoxybenzamide (0.56 g), m.p. 151-153° C. [Elemental analysis: C,60.3; H,6.45; N,6.3%; calculated: C,60.1; H,6.4; N,6.4%].

Workup

  1. customthat is prepared
  2. customat room temperature
  3. stirringstirred at 60° C. for 5 hours
  4. temperatureThe solution is then cooled to room temperature
  5. extractionextracted with ethyl acetate (2×100 mL)
  6. dry with materialThe combined organic extracts are dried over magnesium sulfate
  7. customevaporated
  8. customto give a white solid, which
  9. washeluting with t-butyl methyl ether

Sources & evidence

ORD record
ord-491eb2d7ed8f42a695d7329959ac1fdc
Source dataset
uspto-grants-1999_08
Patent number
US05935978

Reaction notes

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