Benzyl Chloride → HCID 20318585, compound

HRID 866779Notes

Reaction equation

HRID 866779 reaction equation
Cl.[C:2]([NH:6][CH2:7][CH:8]([C:10]1[CH:18]=[C:14]([C:15]([NH2:17])=[O:16])[C:13]([OH:19])=[CH:12][CH:11]=1)[OH:9])([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC(CC)=O>[CH2:26]([O:19][C:13]1[CH:12]=[CH:11][C:10]([CH:8]([OH:9])[CH2:7][NH:6][C:2]([CH3:5])([CH3:3])[CH3:4])=[CH:18][C:14]=1[C:15]([NH2:17])=[O:16])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 12814686HCID 12814686, compound

Product 1

HCID 20318585HCID 20318585, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

5-(2-tert.butylamino-1-hydroxyethyl)-salicylamide hydrochloride (2.0g) in ethyl methyl ketone (50 ml) and anhydrous potassium carbonate (1.5 g) were refluxed together with stirring for 1/2 hour. Benzyl chloride (1.75 g) in ethyl methyl ketone (5 ml) was added dropwise with stirring and the mixture was refluxed for 17 hours. The potassium salts were filtered off and the filtrate was evaporated to dryness in vacuo leaving a cream solid which was crystallised from ethyl acetate to afford 2-(benzyloxy)-5-(2-tert. butylamino-1-hydroxyethyl)-benzamide as colourless needles (1.4g) m.p. 120° C.

Workup

  1. stirringwith stirring
  2. temperaturethe mixture was refluxed for 17 hours
  3. filtrationThe potassium salts were filtered off
  4. customthe filtrate was evaporated to dryness in vacuo
  5. customleaving a cream solid which
  6. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-035100020b4644dfb5eee68b256355f6
Source dataset
uspto-grants-1978_07
Patent number
US04101579

Reaction notes

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