Methanesulfonamide → N-(4-hexadecylamino-2-thiophenecarbonyl)methanesulfonamide

HRID 850990Notes

Reaction equation

HRID 850990 reaction equation
Cl.[CH2:2]([NH:18][C:19]1[CH:20]=[C:21]([C:24](Cl)=[O:25])[S:22][CH:23]=1)[CH2:3][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][CH3:17].[CH3:27][S:28]([NH2:31])(=[O:30])=[O:29]>N1C=CC=CC=1>[CH2:2]([NH:18][C:19]1[CH:20]=[C:21]([C:24]([NH:31][S:28]([CH3:27])(=[O:30])=[O:29])=[O:25])[S:22][CH:23]=1)[CH2:3][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][CH3:17]

Participants

4

Reactant 2

HCID 72879MethanesulfonamideHCID 205036504-Hexadecylamino-2-thiophenecarbonyl chloride hydrochloride

Product 1

HCID 20503666N-(4-hexadecylamino-2-thiophenecarbonyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 25 g. of 4-hexadecylamino-2-thiophenecarbonyl 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 seperated, 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 seperated
  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-9a5bd030495b4dbdb529cc933f2f50ca
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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