Acetyl chloride → HCID 58172481, compound

HRID 889583Notes

Reaction equation

HRID 889583 reaction equation
C(Cl)(=O)C.[NH:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2(O)[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]2)=[CH:6]1>CCO>[NH:16]1[CH2:17][CH2:18][CH:19]=[C:14]([C:7]2[C:8]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:5][CH:6]=2)[CH2:15]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 24758040HCID 24758040, compound

Product 1

HCID 58172481HCID 58172481, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 ml acetylchloride was slowly added to 200 ml of EtOH (−10° C.). After 15 minutes, this solution was added to compound 4 (5 g, 16.3 mmol) and heated to reflux for 1 hour. The mixture was cooled, concentrated and re-dissolved in MeOH. Filtration over 25 g SCX-2 (MeOH followed by 1 N NH3/MeOH) gave the title compound (1.43 g, 7.18 mmol, 44.1%) as amorphous material. 1H-NMR (400 MHz, CDCl3): δ 11.4-10.8 (bs, 1H), 8.32 (dd, J=5 Hz, 2 Hz, 1H), 8.2 (dd, J=8 Hz, 2 Hz, 1H), 7.15 (dd, J=8 Hz, J=5 Hz, 1H), 6.32-6.27 (m, 1H), 3.76-3.72 (m, 2H), 3.10-3.04 (m, 2H), 2.36-2.29 (m, 2H). (TLC MeOH/triethylamine (97/3 Rf 0.25).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. dissolutionre-dissolved in MeOH
  6. filtrationFiltration over 25 g SCX-2 (MeOH followed by 1 N NH3/MeOH)

Sources & evidence

ORD record
ord-8a9ed6d123ed4991ba974db95462b2e8
Source dataset
uspto-grants-2012_08
Patent number
US08252930B2

Reaction notes

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