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

HRID 582771

反応式

HRID 582771 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

反応条件

温度
-30 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8e81096a567346fb902c19695c444b11
出典データセット
uspto-grants-1999_07
特許番号
US05925661

関連ノート

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