Hydrochloric Acid → 2-(Diethylamino)-2'-acetyl-6'-methylacetanilide hydrochloride

HRID 437897Notes

Reaction equation

HRID 437897 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[C:13](=[O:15])[CH3:14])=[O:4].[CH2:16]([NH:18][CH2:19][CH3:20])[CH3:17].[ClH:21]>C1(C)C=CC=CC=1.CCOCC>[ClH:21].[CH2:16]([N:18]([CH2:19][CH3:20])[CH2:2][C:3]([NH:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[C:13](=[O:15])[CH3:14])=[O:4])[CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 214273262-Bromo-2'-acetyl-6'-methylacetanilide

Product 1

HCID 214273302-(Diethylamino)-2'-acetyl-6'-methylacetanilide hydrochloride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4.0 g of 2-bromo-2'-acetyl-6'-methylacetanilide in 60 ml of toluene was added 2.5 g of diethylamine at room temperature. The resultant mixture was stirred at room temperature overnight. The reaction mixture was washed with water, dried over anhydrous sodium sulfate and evaporated to give an oily residue. The residue was dissolved in ether and hydrogen chloride was added to the solution to give crystals. Recrystallization from ethanol-ether gave 2-(diethylamino)-2'-acetyl-6'-methylacetanilide hydrochloride having a melting point of 141° to 143° C.

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated
  4. customto give an oily residue
  5. customto give crystals
  6. customRecrystallization from ethanol-ether

Sources & evidence

ORD record
ord-941eaeb3fd294ad48f320c62ef73f246
Source dataset
uspto-grants-1977_06
Patent number
US04032573

Reaction notes

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