Acetyl chloride → HCID 21947396, compound

HRID 2214642Notes

Reaction equation

HRID 2214642 reaction equation
Cl.[F:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[OH-].[Na+].[C:21](Cl)([CH3:23])=[O:22]>C(Cl)Cl>[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:21](=[O:22])[CH3:23])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 21947523HCID 21947523, compound

Product 1

HCID 21947396HCID 21947396, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bis-(4-fluoro-benzyl)-amine hydrochloride (43 grams, 0.16 mole) was suspended in 200 mL of CH2Cl2. To this was added 730 mL of 1N NaOH. The reaction mixture was stirred vigorously while AcCl (20 mL, 0.28 mole) was slowly added. The reaction was stirred for 0.5 h, then the organic layer separated, washed with 1N HCl, dried over Na2SO4, filtered and the solvent removed under vacuum to yield 24 grams (55% yield) of N,N-bis-(4-fluoro-benzyl)-acetamide as an oil. MS (M+H) calcd for C16H16F2NO: 276.1. found: 276.0. Anal. calcd for C16H15F2NO: C, 69.80; H, 5.49; N, 5.08. found: C, 69.53; H, 5.41; N, 5.06. 1H NMR (500 MHz, DMSO) δ: 2.10 (s, 3), 4.45 (s, 2), 4.50 (s, 2), 7.11–7.27 (overlapping m, 8). 13C NMR (125 MHz, DMSO) δ: 21.34, 50.04, 54.80, 114.90, 115.07, 115.27, 115.45, 128.51, 128.58, 129.57, 129.64, 133.32, 133.34, 133.86, 133.89, 160.25, 160.33, 162.27, 170.22.

Workup

  1. additionwas slowly added
  2. customthe organic layer separated
  3. washwashed with 1N HCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-5bcc1c4bd1664318859396c3c008cbb0
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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