Salicylamide → HCID 21994462, compound

HRID 1977609Notes

Reaction equation

HRID 1977609 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:18][N:19]([CH2:21][CH2:22]Cl)[CH3:20]>O1CCOCC1.O>[CH3:18][N:19]([CH3:20])[CH2:21][CH2:22][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

6

Reactant 3

HCID 5147SalicylamideHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 21994462HCID 21994462, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 2-hydroxy-benzamide (10 g) and potassium carbonate (35.4 g) in dioxane (50 ml) and water (4.5 ml) was added with N,N-dimethyl-2-chlorethylamine hydrochloride (6.5 g). The mixture was heated at 85° C. for 3 hours. The solvent was evaporated off, the resulting residue was poured into 5% HCI and extracted with diethyl ether. The aqueous phase was adjusted to pH with sodium bicarbonate, then extracted with ethyl acetate. The organic layer was dried and evaporated to dryness to give the title compound as a white solid (5.7 g).

Workup

  1. customThe solvent was evaporated off
  2. additionthe resulting residue was poured into 5% HCI
  3. extractionextracted with diethyl ether
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-989f493b399b49509d3a34da3ed64e23
Source dataset
uspto-grants-2001_05
Patent number
US06235738B1

Reaction notes

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