Methanesulfonamide → HCID 20330990, compound

HRID 2057671Notes

Reaction equation

HRID 2057671 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]2[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=2)=[CH:5][CH:4]=1.[CH3:32][S:33]([NH2:36])(=[O:35])=[O:34]>N1C=CC=CC=1>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([NH:36][S:33]([CH3:32])(=[O:35])=[O:34])=[O:28])=[CH:25][CH:24]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 72879MethanesulfonamideHCID 20331330HCID 20331330, compound

Product 1

HCID 20330990HCID 20330990, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 25.2 g. of 4-[13-(4-chlorophenyl)tridec-12-ynylamino]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 and evaporated. Crystallization of the residual white solid from 60% aqueous acetic acid and then from methylene chloride-hexane affords N-{4-[13-(4-chlorophenyl)tridec-12-ynylamino]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. customdried
  6. customevaporated
  7. customCrystallization of the residual white solid from 60% aqueous acetic acid

Sources & evidence

ORD record
ord-317d0d0bdac146ea935a2d5fcd8e758c
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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