Dipropylamine → HCID 13506607, compound

HRID 1766009Notes

Reaction equation

HRID 1766009 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=O)=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17].[CH2:19]([NH:22][CH2:23][CH2:24][CH3:25])[CH2:20][CH3:21]>C1COCC1.C(Cl)(Cl)Cl>[CH2:19]([N:22]([CH2:23][CH2:24][CH3:25])[C:13](=[O:15])[CH2:12][C:9]1[CH:10]=[CH:11][C:6]([OH:5])=[C:7]([N+:16]([O-:18])=[O:17])[CH:8]=1)[CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 8902DipropylamineHCID 24386Thionyl ChlorideHCID 4473644-Hydroxy-3-nitrophenylacetic acid

Product 1

HCID 13506607HCID 13506607, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

Thionyl chloride (50 ml, 680 mmol) was added dropwise to a solution of (4-hydroxy-3-nitrophenyl)acetic acid (25 g, 127 mmol) obtained in 1) in THF (100 ml) at room temperature, and the mixture was heated under reflux for 2 hours. The reaction solution was concentrated, and the resultant residues were dissolved in chloroform (250 ml) and added dropwise over 1 hour to a solution of dipropylamine (35 ml, 255 mmol) in chloroform (300 ml) under cooling with ice-bath. After this addition, the reaction solution was washed with water and aqueous saturated sodium bicarbonate, and the organic layer was dried over anhydrous sodium sulfate and concentrated. The residues were crystallized from ethyl acetate-hexane, whereby N,N-dipropyl-(4-hydroxy-3-nitrophenyl) acetamide (26.5 g) was obtained as crystals with a mp of 55 to 57° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction solution was concentrated
  4. dissolutionthe resultant residues were dissolved in chloroform (250 ml)
  5. temperatureunder cooling with ice-bath
  6. additionAfter this addition
  7. washthe reaction solution was washed with water and aqueous saturated sodium bicarbonate
  8. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe residues were crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9a9026b8f9664ab1a457a05b8e57bcbf
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

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