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Pyridine → HCID 178474481, compound

HRID 275037
Notes
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Reaction equation

HRID 275037 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([Cl:16])[C:9]=1[NH2:10].[C:17]([NH:20][C:21]1[NH:25][N:24]=[C:23]([S:26](Cl)(=[O:28])=[O:27])[N:22]=1)(=[O:19])[CH3:18].[OH-].[Na+]>C(Cl)Cl>[Cl:7][C:8]1[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([Cl:16])[C:9]=1[NH:10][S:26]([C:23]1[N:22]=[C:21]([NH:20][C:17](=[O:19])[CH3:18])[NH:25][N:24]=1)(=[O:27])=[O:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 1165292,6-Dichloro-3-methylanilineHCID 178474479HCID 178474479, compound

Product 1

HCID 178474481HCID 178474481, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A 250 ml, 1-necked flask equipped with a magnetic stirrer and filled with nitrogen gas was charged with 15 ml of dry pyridine and 8.8 g (0.05 mole) of 2,6-dichloro-3-methylaniline. To the stirred solution was added 11.3 g (0.05 mole) of crude 5-acetylamino-3-chlorosulfonyl-1,2,4-triazole over 10-30 minutes. The resulting dark green mixture, which had a mild exotherm during the addition, was heated to 100°-105° C. with stirring for 3-4 hours. It was then dispersed between a mixture of methylene chloride and dilute aqueous sodium hydroxide and the organic layer was removed. Acidification of the aqueous phase and filtraton and drying of the precipitate that formed gave the title sulfonamide as a tan solid melting at 284° (dec.). The yield was 60 percent of theory. A sample of this compound which was recrystallized from a mixture of methanol and water was a pale ivory powder melting at 285°-285.5° C. (dec.) and had the following elemental analysis: Calc. for C11H11Cl2N5O3S %C, 36.3; %H, 3.04; %N, 19.23 Found 36.3; %H, 3.08; %N, 19.65

Workup

  1. customA 250 ml, 1-necked flask equipped with a magnetic stirrer
  2. additionfilled with nitrogen gas
  3. additionduring the addition
  4. temperaturewas heated to 100°-105° C.
  5. customthe organic layer was removed
  6. customAcidification of the aqueous phase and filtraton and drying of the precipitate
  7. customthat formed

Sources & evidence

ORD record
ord-d299c22d67304762a2891dfed43843bd
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05391759

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes