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

HRID 1389100Notes

Reaction equation

HRID 1389100 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 chloride-hexane 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-e91ded5668d4410a8415d25511af86ce
Source dataset
uspto-grants-1981_01
Patent number
US04243609

Reaction notes

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