3'-Aminoacetophenone → HCID 53797596, compound

HRID 1580534Notes

Reaction equation

HRID 1580534 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:11]([C:16]1[CH:26]=[C:25]([C:27]([CH2:30][CH3:31])([CH3:29])[CH3:28])[CH:24]=[CH:23][C:17]=1[O:18][CH2:19][C:20](Cl)=[O:21])([CH2:14][CH3:15])([CH3:13])[CH3:12]>N1C=CC=CC=1>[C:11]([C:16]1[CH:26]=[C:25]([C:27]([CH2:30][CH3:31])([CH3:29])[CH3:28])[CH:24]=[CH:23][C:17]=1[O:18][CH2:19][C:20]([NH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1)=[O:21])([CH2:14][CH3:15])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 74173'-AminoacetophenoneHCID 66612(2,4-Bis(1,1-dimethylpropyl)phenoxy)acetyl chloride

Product 1

HCID 53797596HCID 53797596, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

40 grams (0.1 mol) of N-{α-(2,4-di-tert-amylphenoxy)acetyl} -m-aminoacetophenone (m.p.:135°C), obtained by the reaction between m-aminoacetophenone and α-(2,4-di-tert-amylphenoxy)acetyl chloride in pyridine, was dissolved in 200 ml of anhydrous ethyl ether (placed in a three-necked flask), and 0.5 g of anhydrous aluminum chloride powder was added to this solution followed by ice-cooling (about 0°-5°C) under stirring. 16 grams (0.1 mol) of bromine was added dropwise to this mixture. After the completion of the dropwise addition, the temperature was allowed to rise to room temperature (about 20°-35°C). Stirring was continued until the generation of hydrogen bromide stopped. Thus, white crystals were precipitated.

Sources & evidence

ORD record
ord-e3dff9889de94634aa609c83bdfd0cee
Source dataset
uspto-grants-1976_01
Patent number
US03933500

Reaction notes

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