Pyridine → HCID 14552585, compound

HRID 2248162Notes

Reaction equation

HRID 2248162 reaction equation
[CH3:1][C:2]([CH3:17])=[CH:3][CH2:4][O:5][C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][CH:12]([NH2:14])[CH3:13])=[CH:8][CH:7]=1.N1C=CC=CC=1.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26]>CCOCC>[CH3:17][C:2]([CH3:1])=[CH:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH:12]([NH:14][C:25](=[O:26])[O:27][CH2:28][CH3:29])[CH3:13])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 14552584HCID 14552584, compound

Product 1

HCID 14552585HCID 14552585, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To the above amine (0.86 g, 3.7 mmol) and pyridine (0.64 g, 8.0 mmol ) in 8 ml of ether at 5° is added dropwise over 10 min. ethyl chloroformate (0.43 g, 4.0 mmol) in 2 ml of ether. The mixture is stirred at 5° for 1 hour and is then allowed to warm to RT. Excess ethyl chloroformate is quenched with water and the reaction mixture is poured into water and ether and the aqueous phase is extracted with ether (3X). The combined organic layers are washed with 2N ammonium sulfate, with 10% sodium carbonate, then with water until neural and with brine. The organic layer is dried, filtered, the solvent removed and the product purified by prep. TLC to give ethyl N-{2-[4-(3-methyl-2-butenoxy)phenoxy]-1-methylethyl}carbamate m/s (M+) 307.

Workup

  1. customExcess ethyl chloroformate is quenched with water
  2. additionthe reaction mixture is poured into water and ether
  3. extractionthe aqueous phase is extracted with ether (3X)
  4. washThe combined organic layers are washed with 2N ammonium sulfate, with 10% sodium carbonate
  5. customThe organic layer is dried
  6. filtrationfiltered
  7. customthe solvent removed
  8. customthe product purified by prep

Sources & evidence

ORD record
ord-f18eca2870e34bc89590a5f19b795d70
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

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