Methanesulfonamide → N-{4-[15-(Trifluoromethyl)pentadecylamino]-benzoyl}methanesulfonamide

HRID 1659929Notes

Reaction equation

HRID 1659929 reaction equation
Cl.[F:2][C:3]([F:30])([F:29])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.[CH3:31][S:32]([NH2:35])(=[O:34])=[O:33]>N1C=CC=CC=1>[F:2][C:3]([F:30])([F:29])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:35][S:32]([CH3:31])(=[O:34])=[O:33])=[O:25])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 72879MethanesulfonamideHCID 205493174-[15-(Trifluoromethyl)pentadecylamino]benzoyl chloride hydrochloride

Product 1

HCID 20549394N-{4-[15-(Trifluoromethyl)pentadecylamino]-benzoyl}methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 25.2 g. of 4-[15-(trifluoromethyl)-pentadecylamino]benzoyl chloride hydrochloride and 5.6 g. of methanesulfonamide in 250 ml. of pyridine is stirred under reflux for 2 hours and then concentrated in vacuo. The residue is partitioned between water and diethyl ether; the aqueous layer acidified with 1 N hydrochloric acid, and the organic layer separated, dried over magnesium sulfate and evaporated. Crystallization of the residual white solid from 60% aqueous acetic acid and then from methylene chloride-hexane affords the product as a white solid.

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue is partitioned between water and diethyl ether
  4. customthe organic layer separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customCrystallization of the residual white solid from 60% aqueous acetic acid

Sources & evidence

ORD record
ord-c18c8c2ef65946d288fde015dea94be6
Source dataset
uspto-grants-1981_12
Patent number
US04305959

Reaction notes

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