Acetyl chloride → HCID 25019287, compound

HRID 1785611Notes

Reaction equation

HRID 1785611 reaction equation
Cl.[NH2:2][N:3]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=2)[N:5]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:4]1=[O:26].C(N(CC)CC)C.[C:34](Cl)(=[O:36])[CH3:35]>ClCCl>[C:34]([NH:2][N:3]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([CH3:15])[CH:9]=2)[N:5]([CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[C:4]1=[O:26])(=[O:36])[CH3:35]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 68427637HCID 68427637, compound

Product 1

HCID 25019287HCID 25019287, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 1-amino-3-[2-(4-methoxy-phenyl)ethyl]-4-(3,4-dimethylphenyl)-2-imidazolidinone hydrochloride (300 mg, 0.80 mmol) in dichloromethane (3.0 mL) is cooled in an ice bath and triethylamine (0.26 mL, 1.8 mmol) is added, followed by dropwise addition of acetyl chloride (0.068 mL, 0.96 mmol). The reaction is stirred in the cold for 45 minutes and washed with 0.1 N aqueous HCl, H2O, 10% aqueous NaHCO3, and brine. The organic phase is dried (Na2SO4) and concentrated under reduced pressure. The residue is purified over silica (2.5% methanol/dichloromethane) to afford 237 mg (78% yield) of the desired compound. 1H NMR (CDCl3) δ 9.18 (s, 1H), 7.12 (m, 3H), 7.07 (d, J=8.4 Hz, 2H), 6.83 (d, J=8.4 Hz), 4.41 (t, J=8.4 Hz, 1H), 3.91 (t, J=8.4 Hz, 1H), 3.81 (s, 3H), 3.71 (m, 1H), 3.59 (t, J=8.1 Hz, 1H), 2.94 (m, 1H), 2.80 (m, 1H), 2.67 (m, 1H), 2.29 (s, 6H), 2.09 (s, 3H). MS 382 (MH+). Anal. Calcd. For C22H27N3O3¼H2O: C, 68.46, H, 7.18; N, 10.89. Found: C, 68.72, H, 6.97; N, 10.85.

Workup

  1. washwashed with 0.1 N aqueous HCl, H2O, 10% aqueous NaHCO3, and brine
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified over silica (2.5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-fe5f5e1e24c946f984ca9e9c09b48ce5
Source dataset
uspto-grants-2009_03
Patent number
US07504517B2

Reaction notes

Loading…