Methanesulfonamide → N-[3-fluoro-4-(hexadecylamino)benzoyl]methanesulfonamide

HRID 1156125Notes

Reaction equation

HRID 1156125 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:6](Cl)=[O:7].[CH3:29][S:30]([NH2:33])(=[O:32])=[O:31]>N1C=CC=CC=1>[F:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:6]([NH:33][S:30]([CH3:29])(=[O:32])=[O:31])=[O:7]

Participants

4

Reactant 2

HCID 72879MethanesulfonamideHCID 205364403-Fluoro-4-hexadecylaminobenzoyl chloride hydrochloride

Product 1

HCID 20536472N-[3-fluoro-4-(hexadecylamino)benzoyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 25.2 g. of 3-fluoro-4-(hexadecylamino)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 HCl, and the organic layer separated, dried (MgSO4), and evaporated. Crystallization of the residual white solid from 60% aqueous acetic acid and then from methylene chloridehexane affords N-[3-fluoro-4-(hexadecylamino)benzoyl]methanesulfonamide 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 (MgSO4)
  6. customevaporated
  7. customCrystallization of the residual white solid from 60% aqueous acetic acid

Sources & evidence

ORD record
ord-7b621cbeac60426a90ed7f5cf3c9a96d
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

Loading…