Triethylamine → N-methoxy-N-methyl-4-(pentafluoro-lambda6-sulfanyl)benzamide

HRID 1523310Notes

Reaction equation

HRID 1523310 reaction equation
[F:1][S:2]([F:15])([F:14])([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.Cl.[CH3:17][O:18][NH:19][CH3:20].C(N(CC)CC)C>ClCCl>[CH3:17][O:18][N:19]([CH3:20])[C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([S:2]([F:15])([F:14])([F:13])([F:12])[F:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27792154-(Pentafluorosulfanyl)benzoyl chloride

Product 1

HCID 58360637N-methoxy-N-methyl-4-(pentafluoro-lambda6-sulfanyl)benzamideYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(Pentafluoro-λ6-sulfanyl)benzoyl chloride (1.00 g, 3.751 mmol), O,N-dimethyl-hydroxylamine hydrochloride (0.402 g, 4.13 mmol), and triethylamine (0.835 g, 8.25 mmol) were stirred in dichloromethane for 2 hours at room temperature. The reaction was concentrated in vacuo and diethyl ether added. The solid was collected by filtration and purified by silica gel column chromatography to afford the title compound as a solid (0.557 g, 51% yield).

Workup

  1. concentrationThe reaction was concentrated in vacuo and diethyl ether
  2. additionadded
  3. filtrationThe solid was collected by filtration
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-50c7cfac7e1041dba3a139d5a554d541
Source dataset
uspto-grants-2015_07
Patent number
US09079878B2

Reaction notes

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