Acetyl chloride → HCID 87373563, compound

HRID 1753192Notes

Reaction equation

HRID 1753192 reaction equation
C([Cl:4])(=O)C.[O:5]=[C:6]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[CH2:7][NH:8]C(=O)OC(C)(C)C>CO>[Cl-:4].[Cl-:4].[NH3+:8][CH2:7][C:6]([C:16]1[CH:21]=[CH:20][NH+:19]=[CH:18][CH:17]=1)=[O:5]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 58993186HCID 58993186, compound

Product 1

HCID 87373563HCID 87373563, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Dry MeOH (10 mL) was treated with acetyl chloride (1.8 mL, 25 mmol) at 0° C. under nitrogen. The solution was allowed at room temperature and stirred for 15 minutes before being added to a chilled (ice bath) solution of tert-butyl [2-oxo-2-(pyridin-4-yl)ethyl]carbamate (785 mg, 3.0 mmol) in dry MeOH (10 mL). The resulting yellow solution was allowed at room temperature and stirred for 4 hours and then concentrated in vacuo to give the crude 4-(ammonioacetyl)pyridinium dichloride as a yellow solid (600 mg, yield 96%). The material was carried through without purification. 1H-NMR (400 MHz, d6-DMSO): δ 7.35 (t, 1H, 50.8 Hz), 8.01-8.05 (m, 2H), 8.60 (br s, 2H), 8.93-8.97 (m, 2H).

Workup

  1. customwas allowed at room temperature
  2. additionbefore being added to
  3. customwas allowed at room temperature
  4. stirringstirred for 4 hours
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e86e628217742daa595d0286d9133ec
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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