Pyridine → HCID 13671602, compound

HRID 247544Notes

Reaction equation

HRID 247544 reaction equation
Cl[CH:2]([NH:7][C:8](=[O:16])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[OH:11])[C:3]([Cl:6])([Cl:5])[Cl:4].[F:17][C:18]([F:22])([F:21])[CH2:19][OH:20].N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:4][C:3]([Cl:6])([Cl:5])[CH:2]([NH:7][C:8](=[O:16])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[OH:11])[O:20][CH2:19][C:18]([F:22])([F:21])[F:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 64092,2,2-TrifluoroethanolHCID 129401702-Hydroxy-N-(1,2,2,2-tetrachloroethyl)benzamide

Product 1

HCID 13671602HCID 13671602, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of N-(1,2,2,2-tetrachloroethyl) salicylamide (30 g) in toluene (100 ml) is added dropwise at less than 10° C. to a solution of 2,2,2-trifluoroethanol (10 g) and pyridine (18.6 g) in toluene (150 ml). After the addition, the mixture is stirred at room temperature for a while, and the contents are washed with water and a 1% aqueous solution of sodium hydrogen carbonate. The toluene layer is dehydrated, and the toluene is evaporated under reduced pressure to give the desired N-[2,2,2,-trichloro-1-(2,2,2,-trifluoroethoxy) ethyl]-salicylamide (26 g) represented by the foregoing formula as a colorless viscous mass. This compound gradually solidifies and shows a melting point of 78° to 82° C.

Workup

  1. additionAfter the addition
  2. washthe contents are washed with water
  3. customthe toluene is evaporated under reduced pressure

Sources & evidence

ORD record
ord-98561f82442b4e6c94a4c513c7cfe436
Source dataset
uspto-grants-1987_11
Patent number
US04708953

Reaction notes

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