1-Bromononane → HCID 18707224, compound

HRID 263596Notes

Reaction equation

HRID 263596 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][O:26][CH3:27])=[C:20]([C:28]([OH:30])=[O:29])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[H-].[Na+].Br[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>CN(C)C=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][O:26][CH3:27])=[C:20]([C:28]([O:30][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[O:29])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 3

HCID 127421-BromononaneHCID 24758Sodium hydrideHCID 18707192HCID 18707192, compound

Product 1

HCID 18707224HCID 18707224, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 5 ml of dimethylformamide was dissolved 600 mg of 2-(3,4-diethoxyphenyl)-4-(3-carboxy-4-methoxymethoxyphenyl)thiazole. Thereto was added 56 mg of sodium hydride and 290 mg of 1-bromononane. The mixture was stirred at room temperature for 14 hours. The solvent was removed by distillation. To the residue were added 80 ml of dichloromethane and 30 ml of a 10% aqueous sodium hydroxide solution, and phase separation was conducted. The dichloromethane portion was washed with 20 ml of a saturated aqueous sodium chloride solution, dried and subjected to distillation to remove the solvent. The residue was subjected to silica gel column chromatography. There was obtained, from the dichloromethane layer, 340 mg of 2-(3,4-diethoxyphenyl)-4-(3-nonyloxycarbonyl-4-methoxymethoxyphenyl)thiazole as a colorless oily substance.

Workup

  1. customThe solvent was removed by distillation
  2. additionTo the residue were added
  3. custom80 ml of dichloromethane and 30 ml of a 10% aqueous sodium hydroxide solution, and phase separation
  4. washThe dichloromethane portion was washed with 20 ml of a saturated aqueous sodium chloride solution
  5. customdried
  6. distillationsubjected to distillation
  7. customto remove the solvent

Sources & evidence

ORD record
ord-963edbe6759c448a90070d2af4a3752c
Source dataset
uspto-grants-1997_07
Patent number
US05643932

Reaction notes

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