Acetyl chloride → HCID 46938718, compound

HRID 1866554Notes

Reaction equation

HRID 1866554 reaction equation
[C:1](Cl)(=O)C.ClCC([NH:9][C:10]([CH3:23])([CH3:22])[CH2:11][C:12]1[CH:13]=[C:14]([CH2:18][C:19]([OH:21])=[O:20])[CH:15]=[CH:16][CH:17]=1)=O>CO>[CH3:1][O:21][C:19](=[O:20])[CH2:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([CH2:11][C:10]([NH2:9])([CH3:23])[CH3:22])[CH:13]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 46938812{3-[2-(2-Chloroacetamido)-2-methylpropyl]phenyl}acetic acid

Product 1

HCID 46938718HCID 46938718, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (154.5 g, 1.97 mol) was added to a solution of {3-[2-(2-chloro-acetylamino)-2-methyl-propyl]-phenyl}-acetic acid (preparation 48), (20 g, 0.66 mol) in methanol (350 mL) and the mixture was heated under reflux for 18 hours. The reaction mixture was then concentrated in vacuo to afford the title compound as a brown oil in 87% yield, 154.5 g. 1H NMR (300 MHz, CDCl3) δ: 7.22 (1H, m), 7.18-7.05 (3H, m), 3.71 (3H, s), 3.58 (2H, s), 2.62 (2H, s), 1.12 (6H, s) ppm; GCMS m/z 206 [M−H]−.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-702ef986f5884c35bdea60c00ed69659
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

Loading…