Hydrochloric Acid → 8-(p-Nitrobenzamido)-1,3,6-naphthalenetrisulfonic acid trisodium salt

HRID 1447569

반응식

HRID 1447569 반응식
[Na+:1].[Na+].[Na+].[NH2:4][C:5]1[CH:6]=[C:7]([S:23]([O-:26])(=[O:25])=[O:24])[CH:8]=[C:9]2[C:14]=1[C:13]([S:15]([O-:18])(=[O:17])=[O:16])=[CH:12][C:11]([S:19]([O-:22])(=[O:21])=[O:20])=[CH:10]2.[OH-].[Na+].[N+:29]([C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1)([O-:31])=[O:30].Cl>O.C(OCC)C>[Na+:1].[Na+:1].[Na+:1].[N+:29]([C:32]1[CH:33]=[CH:34][C:35]([C:36]([NH:4][C:5]2[CH:6]=[C:7]([S:23]([O-:26])(=[O:25])=[O:24])[CH:8]=[C:9]3[C:14]=2[C:13]([S:15]([O-:18])(=[O:17])=[O:16])=[CH:12][C:11]([S:19]([O-:22])(=[O:20])=[O:21])=[CH:10]3)=[O:37])=[CH:39][CH:40]=1)([O-:31])=[O:30]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 14798Sodium HydroxideHCID 1018991,3,6-Naphthalenetrisulfonic acid, 8-amino-, sodium salt (1:?)

생성물 1

HCID 1317113678-(p-Nitrobenzamido)-1,3,6-naphthalenetrisulfonic acid trisodium salt수율 238.6%

시약·촉매·용매 2

HCID 962Water용매2회HCID 3283Diethyl Ether용매

실험 절차

To a solution of 27.0 g of 8-amino-1,3,6-naphthalenetrisulfonic acid trisodium salt in 100 ml of water and 60 ml of N sodium hydroxide is added 22.5 g of p-nitrobenzoyl chloride and 30 ml of diethyl ether. The reaction mixture is shaken in a separatory funnel for about 15 minutes, and another 60 ml portion of base is added. After shaking for 15 minutes the procedure is repeated with two additional 60 ml portions of base. The reaction mixture is acidified with 7.5 ml of concentrated hydrochloric acid and diluted with 250 ml of water, then extracted 9 times with 300 ml portions of ether. The aqueous phase is neutralized with 5 N sodium hydroxide and allowed to stand overnight at room temperature, then is filtered through diatomaceous earth. The filtrate is concentrated to a low volume in vacuo at 55°-60° C. The crystalline solid formed is collected by filtration, washed and slurried with absolute ethyl alcohol to yield 28.6 g of 8-(p-nitrobenzamido)-1,3,6-naphthalenetrisulfonic acid trisodium salt.

후처리

  1. additionanother 60 ml portion of base is added
  2. stirringAfter shaking for 15 minutes the procedure
  3. extractionextracted 9 times with 300 ml portions of ether
  4. waitto stand overnight at room temperature
  5. filtrationis filtered through diatomaceous earth
  6. concentrationThe filtrate is concentrated to a low volume in vacuo at 55°-60° C
  7. customThe crystalline solid formed
  8. filtrationis collected by filtration
  9. washwashed

출처 및 근거

ORD 기록
ord-c0b86ce9c7534229bdf2c26b9e7497de
출처 데이터셋
uspto-grants-1979_12
특허 번호
US04177209

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