Methyl Ethyl Ketone → Bis(p-diethylaminophenyl)Methoxy Acetanilide

HRID 66931Notes

Reaction equation

HRID 66931 reaction equation
[CH2:1]([N:3]([C:6]1[CH:24]=[CH:23][C:9]([CH:10]([OH:22])[C:11]2[CH:16]=[CH:15][C:14]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].[C:25]([NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:28])[CH2:26]O.C(C(C)=O)C>CS(O)(=O)=O.CN(C)C(=N)N(C)C.CCCCCC>[CH2:18]([N:17]([CH2:20][CH3:21])[C:14]1[CH:15]=[CH:16][C:11]([CH:10]([C:9]2[CH:23]=[CH:24][C:6]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][CH:8]=2)[O:22][CH2:26][C:25]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:28])=[CH:12][CH:13]=1)[CH3:19]

Participants

7

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 672574,4'-Bis(diethylamino)benzhydryl alcoholHCID 2642602-Hydroxy-N-phenylacetamide

Product 1

HCID 70532432Bis(p-diethylaminophenyl)Methoxy Acetanilide

Reagents, catalysts & solvents 3

HCID 6395Methanesulfonic AcidCatalystHCID 664601,1,3,3-TetramethylguanidineCatalystHCID 8058HexaneSolvent

Procedure

A solution of 4,4'-bis(N,N-diethylamino)benzhydrol (11.0 g, 0.034 mole), glycolanilide (5.1 g, 0.034 mole), 37.5 ml of methyl ethyl ketone, 112.5 ml of n-hexane, and 7 drops of methanesulfonic acid was refluxed for about 2 hours, removing water as formed. The solution was then treated with 5 drops of tetramethyl-guanidine and filtered hot. On cooling, the filtrate yielded a tan precipitate. The precipitate was filtered, washed with n-hexane, and dried. The pale yellow solid was recrystallized from 80 ml of methylcyclohexane and 450 ml of acetone to give a solid product, mp 123°-125° C.

Workup

  1. customremoving water
  2. customas formed
  3. filtrationfiltered hot
  4. temperatureOn cooling
  5. customthe filtrate yielded a tan precipitate
  6. filtrationThe precipitate was filtered
  7. washwashed with n-hexane
  8. customdried
  9. customThe pale yellow solid was recrystallized from 80 ml of methylcyclohexane and 450 ml of acetone
  10. customto give a solid product, mp 123°-125° C.

Sources & evidence

ORD record
ord-dabc8e8ebde44ff186e57f0b792aa794
Source dataset
uspto-grants-1982_08
Patent number
US04343939

Reaction notes

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