Hydrochloric Acid → Salicylamide

HRID 247545Notes

Reaction equation

HRID 247545 reaction equation
ClC(Cl)(Cl)CO.ClC([NH:13][C:14](=[O:22])[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[OH:17])C(Cl)(Cl)Cl.Cl>C1(C)C=CC=CC=1>[C:14]([NH2:13])(=[O:22])[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[OH:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8259TrichloroethanolHCID 129401702-Hydroxy-N-(1,2,2,2-tetrachloroethyl)benzamide

Product 1

HCID 5147SalicylamideYield 272.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution composed of 2,2,2-trichloroethanol (30 g), N-(1,2,2,2-tetrachloroethyl) salicylamide (30 g) and toluene (200 ml) is refluxed until the generation of hydrogen chloride ceases (for about 5 to 8 hours). The reaction mixture is cooled to room temperature. The toluene layer is washed with water and dehydrated, and toluene is evaporated under reduced pressure to give the desired N-8 2,2,2-trichloro-1-(2,2,2-trichloroethoxy)-ethyl]salicylamide (37 g) represented by the foregoing formula as colorless crystals. mp. 111°-114° C.

Workup

  1. washThe toluene layer is washed with water
  2. customtoluene is evaporated under reduced pressure

Sources & evidence

ORD record
ord-3e5b45c45a7c44ce86cd38507e1e61de
Source dataset
uspto-grants-1987_11
Patent number
US04708953

Reaction notes

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