Triethylamine → HCID 19029315, compound

HRID 2256293Notes

Reaction equation

HRID 2256293 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:22])[C:9](=[O:21])[CH2:10][CH:11]([CH2:18][CH2:19][OH:20])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:22])[C:9](=[O:21])[CH2:10][CH:11]([CH2:18][CH2:19][O:20][S:31]([CH3:30])(=[O:33])=[O:32])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19029350HCID 19029350, compound

Product 1

HCID 19029315HCID 19029315, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-Chlorophenyl)-beta-(2-hydroxyethyl)-N-methyl-benzenepropanamide (1.25 g) in CH2Cl2 (25 mL) was cooled to -5° to -10° C. and treated sequentially with Et3N (0.497 g), and methanesulfonyl chloride (0.563 g). After two hours the reaction mixture was washed with water (3×25 mL), sat. NaHCO3 (20 mL) and the organic layer separated, dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound (1.44 g).

Workup

  1. washAfter two hours the reaction mixture was washed with water (3×25 mL), sat. NaHCO3 (20 mL)
  2. customthe organic layer separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ffd1cedb7ff42248e364cb1fa8e298f
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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