Acetyl chloride → HCID 67106715, compound

HRID 2357116Notes

Reaction equation

HRID 2357116 reaction equation
[Cl-].[OH:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][C:13]2[N:14]=[CH:15][NH2+:16][CH:17]=2)=[CH:5][CH:4]=1.[C:18]([Cl:21])(=[O:20])[CH3:19]>FC(F)(F)C(O)=O>[Cl-:21].[C:18]([O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][C:13]2[N:14]=[CH:15][NH2+:16][CH:17]=2)=[CH:5][CH:4]=1)(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 178515463HCID 178515463, compound

Product 1

HCID 67106715HCID 67106715, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-(6-hydroxy-indan-1-ylmethyl)-1H-imidazol-1-ium chloride (100 mg, 0.399 mmol) was dissolved in 1 ml of trifluoroacetic acid (TFA) and acetic acid chloride (0.510 mmol) was added. The mixture was stirred at room temperature for 24 h. TFA was evaporated and the residue was dissolved in water and made basic with 2 M NH3 (aq.). The aqueous phase was extracted with dichloromethane (DCM). The combined extracts were dried (Na2SO4) and evaporated. The residue was dissolved in diethyl ether and the solution was saturated with dry HCl gas. The precipitate was filtered and dried under vacuum. Yield 105 mg (82%) of a white hygroscopic solid. 1H NMR (CDCl3, TMS): δ 1.72 (m, 1H), 2.18-2.26 (m, 4H), 2.72-2.87 (m, 3H), 3.17 (dd, 1H), 3.56 (qui, 1H), 6.85 (m, 2H), 6.92 (s, 1H), 7.16 (d, 1H), 8.61 (s, 1H), 14.44 (s, 2H). 13C NMR (CDCl3, TMS): δ 21.11, 29.60, 30.46, 31.68, 43.93, 115.72, 117.00, 120.29, 125.33, 132.32, 132.40, 141.37, 146.32, 149.39, 170.11. HPLC-MS (EI): m/z=257.2 ((M+H)+—Cl−. Anal.—Calc. for C15H16N2O2.HCl.0.2CH2Cl2: C, 58.94; H, 5.66; N, 9.04. Found C, 58.66; H, 5.78; N, 8.83.

Workup

  1. customTFA was evaporated
  2. dissolutionthe residue was dissolved in water
  3. extractionThe aqueous phase was extracted with dichloromethane (DCM)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. customevaporated
  6. dissolutionThe residue was dissolved in diethyl ether
  7. filtrationThe precipitate was filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-d13d4bdcc7184f12802b2ac87c774fd5
Source dataset
uspto-grants-2010_07
Patent number
US07759496B2

Reaction notes

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