Pyridine → HCID 67072557, compound

HRID 45179Notes

Reaction equation

HRID 45179 reaction equation
[F:1][C:2]1[C:3]([CH3:17])=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][NH:6][CH2:7][CH:8]([O:11][CH3:12])[O:9][CH3:10].N1C=CC=CC=1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>ClCCl>[F:1][C:2]1[C:3]([CH3:17])=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][N:6]([S:30]([C:27]1[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=1)(=[O:32])=[O:31])[CH2:7][CH:8]([O:9][CH3:10])[O:11][CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 67075419HCID 67075419, compound

Product 1

HCID 67072557HCID 67072557, compoundYield 110.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

3,4-Difluoro-2-methylbenzyl-2,2-dimethoxyethylamine (41, 37.8 g) was dissolved in dichloromethane (100 mL). Pyridine (42 mL) was added. At 0° C. a solution of p-toluenesulphonyl chloride (36.8 g, 193 mmol) in dichloromethane was added dropwise. The reaction was allowed to warm to room temperature and stirring continued until conversion was complete. For workup, the reaction mixture was diluted with dichloromethane (100 mL) and extracted twice with 1.5M hydrochloric acid, twice with sodium bicarbonate solution and once with brine. The organic layer was dried over magnesium sulphate, evaporated to dryness to give crude product as an orange oil (68.3 g). This was used without further purification.

Workup

  1. extractionextracted twice with 1.5M hydrochloric acid, twice with sodium bicarbonate solution and once with brine
  2. dry with materialThe organic layer was dried over magnesium sulphate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-14e47d9674424e41b096450c903d3f6c
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

Loading…