Hydrochloric Acid → HCID 20039936, compound

HRID 1762879Notes

Reaction equation

HRID 1762879 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.CN(C)C1C=CC=CC=1.[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](Cl)=[O:26].Cl>CC(C)=O>[Br:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([N:2]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)[CH3:1])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 5931n-Methyl-p-aminophenolHCID 898486-Bromohexanoyl chloride

Product 1

HCID 20039936HCID 20039936, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 69 g (0.56 mol) of 4-methylaminophenol and 73.9 g (0.61 mol) of N,N-dimethylaniline in about 1.5 L of acetone was stirred mechanically under nitrogen in a 3 L flask. A solution of 119.6 g (0.56 mol) of 6-bromohexanoyl chloride in 100 mL of acetone was added as rapidly as the exotherm would allow at about 40° C. The reaction was refluxed for 2 hours on a steam bath, allowed to cool and poured into a solution of about 560 mL of 2N HCl in 2 L of ice. The aqueous solution was extracted twice with ethyl acetate and the ethyl acetate extracts were combined and dried over magnesium sulfate. The ethyl acetate solution was stripped to dryness under high vacuum to yield 143.4 g (85%) of greenish-white, low melting, solid 6-bromo-N-(4-hydroxyphenyl)-N-methylhexanamide.

Workup

  1. customwould allow at about 40° C
  2. temperatureThe reaction was refluxed for 2 hours on a steam bath
  3. temperatureto cool
  4. extractionThe aqueous solution was extracted twice with ethyl acetate
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-cfa43fffa79b439b895604f3dfa612bd
Source dataset
uspto-grants-1989_05
Patent number
US04835180

Reaction notes

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