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Acetone → N,N'-diphenyl-N,N'-bis(phenylmethyl)-[1,1'-biphenyl]-4,4'-diamine

HRID 1679086
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HRID 1679086 반응식
[OH-].[K+].[C:3]1([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[CH:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[CH3:43]C(C)=O>>[C:23]1([N:22]([CH2:43][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:19]2[CH:20]=[CH:21][C:16]([C:13]3[CH:14]=[CH:15][C:10]([N:9]([C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:11][CH:12]=3)=[CH:17][CH:18]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 180AcetoneHCID 241BenzeneHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 68280N,N'-Diphenylbenzidine

생성물 1

HCID 14716224N,N'-diphenyl-N,N'-bis(phenylmethyl)-[1,1'-biphenyl]-4,4'-diamine수율 81%

실험 절차

Into a 1000 milliliter round bottom three-necked flask fitted with a magnetic stirrer and a dropping funnel which is flushed with argon, is placed 500 milliliters of anhydrous dimethylsulfoxide (DMSO). Then 100.8 grams (1.8 moles) of powdered potassium hydroxide is added to the flask. The mixture is then stirred for 15 minutes. Then 100.8 grams (0.3 moles) of N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine is added to the mixture. The mixture is now a deep red heterogeneous mixture. The mixture is then stirred at room temperature for 2 hours. Then 200 grams (1.2 moles) of benzyl bromide is added portionwise to the mixture. The mixture is intermittently cooled in order to maintain the temperature between 20° and 40° C. The mixture is then stirred for 2 hours. The mixture becomes brown in color. The mixture is then poured into 1000 milliliters of benzene. The mixture is then extracted with water 4 times using about 2.5 liters of water each time. The mixture is then dried with magnesium sulfate. The benzene is then evaporated from the mixture leaving a black sludge residue. To this add 1 liter of acetone and heat to reflux for about 10 minutes. Let the mixture cool and filter the red solid from the mixture. Then column chromatrograph using Woelm neutral alumina, evaporate eluent. Then wash residue with methanol and dry. This yields 90 grams of white crystals of N,N'-diphenyl-N,N'-bis-(phenylmethyl)-[1,1'-biphenyl]-4,4'-diamine with a melting point of from 141° to 142° C. Additional products may be recovered from the column which equals 35 grams. The total yield is 81 percent.

후처리

  1. customInto a 1000 milliliter round bottom three-necked flask fitted with a magnetic stirrer and a dropping funnel which
  2. customis flushed with argon
  3. stirringThe mixture is then stirred at room temperature for 2 hours
  4. temperatureThe mixture is intermittently cooled in order
  5. temperatureto maintain the temperature between 20° and 40° C
  6. stirringThe mixture is then stirred for 2 hours
  7. extractionThe mixture is then extracted with water 4 times
  8. dry with materialThe mixture is then dried with magnesium sulfate
  9. customThe benzene is then evaporated from the mixture
  10. customleaving a black sludge residue
  11. temperatureto reflux for about 10 minutes
  12. temperaturecool
  13. filtrationfilter the red solid from the mixture
  14. customevaporate eluent
  15. dry with materialThen wash residue with methanol and dry
  16. customof from 141° to 142° C
  17. customAdditional products may be recovered from the column which

출처 및 근거

ORD 기록
ord-3619931bebc84e2dbb36111ab05267df
출처 데이터셋
uspto-grants-1978_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04078925

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