Sodium Chloride → HCID 131717897, compound

HRID 248018Notes

Reaction equation

HRID 248018 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](Cl)=[O:9].[CH2:11]([O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32]N)=[CH:28][CH:27]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(=O)(O)[O-].[Na+].[Cl-].[Na+].C([N:43](CC)CC)C>C(Cl)Cl.O>[CH2:11]([O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:4]2[C:3]([C:8]([NH2:43])=[O:9])=[N:2][CH:7]=[CH:6][CH:5]=2)=[CH:28][CH:27]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 516892Sodium BicarbonateHCID 117234984-(Tetradecyloxy)benzenemethanamine

Product 1

HCID 131717897HCID 131717897, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a room temperature suspension of 6.72 g of product from Example 114 in 200 ml methylene chloride is added, dropwise over 15 minutes, 10.05 g of product from Example 99 dissolved in 160 ml of methylene chloride. The reaction is stirred at room temperature for 10 minutes, followed by the dropwise addition of 12.73 g of triethylamine. The solution is stirred at room temperature for 19 hours, poured into a solution consisting of equal volumes saturated sodium bicarbonate, saturated sodium chloride and water, and extracted with 50/50 chloroform/methylene chloride. The organic layers are washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel: 25% ethyl acetate/hexane) to give 10.75 g of the desired product as pale yellow crystals.

Workup

  1. additionis added, dropwise over 15 minutes
  2. stirringThe solution is stirred at room temperature for 19 hours
  3. additionpoured into a solution
  4. extractionextracted with 50/50 chloroform/methylene chloride
  5. washThe organic layers are washed with saturated sodium chloride
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography (silica gel: 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1ae295265aa6400ba8d1ad364319bf4c
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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