4-Aminobenzophenone → 4-(4-Chloro-1,2-diphenyl-but-1-enyl)phenylamine

HRID 1368948Notes

Reaction equation

HRID 1368948 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)=[CH:4][CH:3]=1.[Cl:16][CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O>O1CCCC1.C(=O)([O-])[O-].[K+].[K+].[Zn]>[Cl:16][CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 143464-AminobenzophenoneHCID 702953-Chloropropiophenone

Product 1

HCID 695444994-(4-Chloro-1,2-diphenyl-but-1-enyl)phenylamine

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×HCID 11430Potassium CarbonateSolvent

Conditions

Temperature
-10 °C

Procedure

Zinc (10.0 g, 0.154 mol) and tetrahydrofuran (THF) (120 ml) is added to the reaction vessel and cooled to −10° C. To the mixture is added dropwise titan tetrachloride (14.4 g, 0.076 mol) at about −10° C. After the addition is completed the mixture is refluxed for two hours. Then it is cooled to 40° C. and (4-Aminophenyl)phenyl-methanone (5.1 g, 0.0258 mol) and 3-chloropropiophenone (4.36 g, 0.0258 mol) are dissolved in THF (50 ml) and added to the mixture. Refluxing is continued for additional 3.5 hours. The cooled reaction mixture is poured in aqueous potassium carbonate solution (14 g K2CO3+140 ml water) and allowed to stand over night. The mixture is filtered and the precipitate is washed three times with THF. The filtrate is evaporated to dryness. The residue is dissolved in ethyl acetate and washed with water. Yield 9.6 g Z-isomer being the only isomer.

Workup

  1. additionAfter the addition
  2. temperatureis refluxed for two hours
  3. temperatureThen it is cooled to 40° C.
  4. additionadded to the mixture
  5. temperatureRefluxing
  6. customThe cooled reaction mixture
  7. waitto stand over night
  8. filtrationThe mixture is filtered
  9. washthe precipitate is washed three times with THF
  10. customThe filtrate is evaporated to dryness
  11. dissolutionThe residue is dissolved in ethyl acetate
  12. washwashed with water

Sources & evidence

ORD record
ord-8d379ca324484213b44fb74b91f6d854
Source dataset
uspto-grants-2003_06
Patent number
US06576645B1

Reaction notes

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