N-ethyl-N-(oxan-4-yl)carbamoyl chloride → N-ethyl-N-(tetrahydro-2H-pyran-4-yl)-4-(2-chlorophenyl)-4,5-dihydro-1H-tetrazol-5-one-1-carboxamide

HRID 650866Notes

Reaction equation

HRID 650866 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[N:11]=[N:10][NH:9]1.[CH2:14]([N:16]([CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:17](Cl)=[O:18])[CH3:15]>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[CH2:14]([N:16]([CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:17]([N:11]1[C:12](=[O:13])[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:9]=[N:10]1)=[O:18])[CH3:15]

Participants

5

Reactant 2

HCID 11127103N-ethyl-N-(oxan-4-yl)carbamoyl chlorideHCID 178518972HCID 178518972, compound

Product 1

HCID 11013583N-ethyl-N-(tetrahydro-2H-pyran-4-yl)-4-(2-chlorophenyl)-4,5-dihydro-1H-tetrazol-5-one-1-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

3.7 g (19 mmol) of 1-(2-chlorophenyl)-1,2-dihydro-5H-tetrazol-5-one, 3.6 g (19 mmol) of N-ethyl-N-(tetrahydro-2H-pyran-4-yl)carbamoyl chloride and 2.6 g (21 mmol) of 4-dimethylaminopyridine in 150 ml of toluene were heated under reflux for 5 hours. The organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (eluent hexane/ethyl acetate 2:1). Yield 5.5 g. 1H NMR (270 MHz, in CDCl3): δ=1.20-1.40 (m, 3H), 1.80-2.05 (m, 4H), 3.30-3.60 (m, 4H), 3.70-4.50 (m, 3H), 7.40-7.60 (m, 4H).

Workup

  1. temperatureunder reflux for 5 hours
  2. washThe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent hexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-f4e2ad08a4a94f6a8acac5d84d95d13b
Source dataset
uspto-grants-2001_08
Patent number
US06277790B1

Reaction notes

Loading…