4-Iodotoluene → 4,4'-Ditolylaminobenzophenon

HRID 326964Notes

Reaction equation

HRID 326964 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1>[Cu].ClC1C=CC=CC=1Cl>[C:5]1([CH3:6])[CH:15]=[CH:16][CH:2]=[CH:3][C:4]=1[NH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH3:17])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 122074-IodotolueneHCID 691494,4'-Diaminobenzophenone

Product 1

HCID 1317182694,4'-DitolylaminobenzophenonYield 277.8%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
180 °C

Procedure

4.4 g of 4,4'-diaminobenzophenon, 30.9 g of P-iodotoluene, 19.5 g of potassium carbonate anhydride and 10 g of copper powder were added to 70 ml of o-dichlorobenzene, and the mixture thus obtained was refluxed with stirring for twenty-four hours at 180° C. After the reaction, the mixture was filtered and washed with ethyl acetate. Then, the mixture was separated by silica gel column chromatography using chloroform, thereby obtaining 11.3 g of 4,4'-ditolylaminobenzophenon.

Workup

  1. customthe mixture thus obtained
  2. temperaturewas refluxed
  3. customAfter the reaction
  4. filtrationthe mixture was filtered
  5. washwashed with ethyl acetate
  6. customThen, the mixture was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-fa6ea7ea9d35492882e58c20343a5601
Source dataset
uspto-grants-1993_12
Patent number
US05271979

Reaction notes

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