Water → 2,2,2-Trifluoroethoxybenzamide

HRID 1262637Notes

Reaction equation

HRID 1262637 reaction equation
[NH2:1]CC1C=CC=CN=1.C(=O)([O-])[O-].[Na+].[Na+].C(O[C:23]1[CH:24]=[CH:25][C:26]([O:32][CH2:33][C:34]([F:37])([F:36])[F:35])=[C:27]([CH:31]=1)[C:28](Cl)=[O:29])C1C=CC=CC=1.O>C1C=CC=CC=1.C(OCC)C>[F:35][C:34]([F:37])([F:36])[CH2:33][O:32][C:26]1[CH:25]=[CH:24][CH:23]=[CH:31][C:27]=1[C:28]([NH2:1])=[O:29]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 195092-PyridinemethanamineHCID 130371795-Benzyloxy-2-(2,2,2-trifluoroethoxy)benzoyl chloride

Product 1

HCID 190095772,2,2-Trifluoroethoxybenzamide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3.2 g (0.0299 mole) of 2-aminomethylpyridine and 12.1 g (0.114 mole) of sodium carbonate in 100 ml of benzene is added dropwise a solution of 9.8 g (0.0285 mole) of 5-benzyloxy-2-(2,2,2-trifluoroethoxy)benzoyl chloride in 30 ml benzene. The mixture is stirred for about 16 hours at room temperature. Water and diethyl ether are added. The ether layer is separated, washed with water, then with saturated aqueous sodium chloride solution. The solution is dried over magnesium sulfate, and the magnesium sulfate is removed by filtration. The filtrate is evaporated to provide a white solid, 5-benzyloxy-N-(2-pyridylmethyl)-2-(2,2,2-trifluoroethoxybenzamide. The infrared and nuclear magnetic resonance spectra of this product are consistent with the assigned structure.

Workup

  1. customThe ether layer is separated
  2. washwashed with water
  3. dry with materialThe solution is dried over magnesium sulfate
  4. customthe magnesium sulfate is removed by filtration
  5. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-364bd61226554d0cafe7f47f15056cd9
Source dataset
uspto-grants-1984_06
Patent number
US04452983

Reaction notes

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