Acetyl chloride → HCID 69473042, compound

HRID 853793Notes

Reaction equation

HRID 853793 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[CH:5][CH:4]=1.[C:20](Cl)(=[O:22])[CH3:21]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[C:20](=[O:22])[CH3:21])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 10729848(4-Methoxy-phenyl)-[2-(3-methoxy-phenyl)-ethyl]-amine

Product 1

HCID 69473042HCID 69473042, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(4-Methoxy-phenyl)-[2-(3-methoxy-phenyl)-ethyl]-amine (3.87 mmol) and acetyl chloride (4.26 mmol) were reacted ethyl acetate (50 mL). After 18 hours, the reaction was poured into ice (150 mL) and the organic extract was dried over sodium sulfate, filtered through celite and concentrated. The title compound (0.60 g) was obtained after silica gel chromatography (eluant: gradient from 10% to 40% ethyl acetate-hexane); MS: 300.4 (MH+); HPLC tR: 2.65 min; TLC Rf: 0.19 (ethyl acetate-hexane 2:3).

Workup

  1. extractionthe organic extract
  2. dry with materialwas dried over sodium sulfate
  3. filtrationfiltered through celite and
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-77d675665a5749a6b58c8f155a3d523d
Source dataset
uspto-grants-2007_08
Patent number
US07256201B2

Reaction notes

Loading…