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Hydrochloric Acid → n-(2-Bromo-5-isopropyl-4-nitrophenyl)-4-methylbenzenesulphonamide

HRID 582771
Notes
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Reaction equation

HRID 582771 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:21]([Mg]Cl)([CH3:23])[CH3:22].[Br:26]Br.Cl>C1COCC1.CCOCC.O.C(N(CC)CC)C>[Br:26][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]([CH:21]([CH3:23])[CH3:22])=[CH:6][C:7]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 69772Benzenesulfonamide, 4-methyl-N-(4-nitrophenyl)-HCID 178418918HCID 178418918, compound

Product 1

HCID 22111869n-(2-Bromo-5-isopropyl-4-nitrophenyl)-4-methylbenzenesulphonamide

Reagents, catalysts & solvents 4

HCID 962
Water
Solvent
HCID 3283Diethyl EtherSolvent
HCID 8028TetrahydrofuranSolvent
HCID 8471TriethylamineSolvent

Conditions

Temperature
-30 °C

Procedure

A solution of 23.47 g of N-(4-nitrophenyl)-4-methylbenzenesulphonamide in 230 ml of THF is cooled to -30° C., 100 ml of a 2M solution of isopropylmagnesium chloride in ether is added and the mixture is left stirring for 30 minutes at -30° C. 10.3 ml of bromine are then added at -30° C., the mixture is left stirring for 15 minutes at this temperature and the temperature is then allowed to rise to 20° C. 55 ml of triethylamine are then added and the mixture is left stirring for 1 hour at RT. Water is added, the mixture is acidified to pH 3-4 by adding 10% HCl solution, the organic phase is separated after settling has taken place, the aqueous phase is extracted with ether and the combined organic phases are dried over Na2SO4. The organic phase is stirred in the presence of animal charcoal, filtered and concentrated under vacuum. The residue is taken up in EtOH and the crystallized product formed is drained. 11.6 g of the expected product are obtained, m.p.=132° C.

Workup

  1. waitthe mixture is left
  2. waitthe mixture is left
  3. stirringstirring for 15 minutes at this temperature
  4. customto rise to 20° C
  5. waitthe mixture is left
  6. stirringstirring for 1 hour at RT
  7. customthe organic phase is separated after settling
  8. extractionthe aqueous phase is extracted with ether
  9. dry with materialthe combined organic phases are dried over Na2SO4
  10. stirringThe organic phase is stirred in the presence of animal charcoal
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum
  13. customthe crystallized product formed

Sources & evidence

ORD record
ord-8e81096a567346fb902c19695c444b11
Source dataset
uspto-grants-1999_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05925661

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes