Dimethylformamide → HCID 53949824, compound

HRID 1608544Notes

Reaction equation

HRID 1608544 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].CN(C)C=O.S(Cl)(Cl)=O.[CH2:23]([NH2:41])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:23]([NH:41][C:9](=[O:11])[C:8]1[CH:7]=[CH:6][C:5]([O:4][C:1](=[O:3])[CH3:2])=[CH:13][CH:12]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 15793OctadecylamineHCID 16865Benzoic acid, 4-(acetyloxy)-HCID 24386Thionyl Chloride

Product 1

HCID 53949824HCID 53949824, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

Under a nitrogen atmosphere, 4-acetoxybenzoic acid (100.0 g) and N,N-dimethylformamide (3 ml) were suspended in chloroform (500 ml) and thereto was added dropwise thionyl chloride (79.2 g) for a period of about 30 minutes. After completion of the addition, the suspension was refluxed with heating for 1 hour to prepare the corresponding acid chloride. The reaction mixture was cooled and thereto were added n-octadecylamine (149.6 g) and triethylamine (67.4 g), followed by refluxing with heating for 3 hours. The reaction mixture was cooled to room temperature to precipitate a white crystal. This crystal was filtered off under reduced pressure and washed with distilled water and then recrystallized from isopropanol to obtain N-n-octadecyl-4-acetoxybenzamide (206.0 g). Yield 86%; m.p. 106° C. This was suspended in 1,4-dioxane (1000 ml) and thereto was added aqueous KOH solution 50%) (160.7 g). The reaction mixture was kept at 40°-45° C. and the reaction was allowed to proceed for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and thereto was added dilute hydrochloric acid to precipitate a white crystal, which was filtered off under reduced pressure. This crystal was washed with distilled water and recrystallized from chloroform to obtain the desired product (137.6 g). Yield 74 %; m.p. 105° C.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe suspension was refluxed
  3. temperaturewith heating for 1 hour
  4. temperatureThe reaction mixture was cooled
  5. temperatureby refluxing
  6. temperaturewith heating for 3 hours
  7. customto precipitate a white crystal
  8. filtrationThis crystal was filtered off under reduced pressure
  9. washwashed with distilled water
  10. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-2a7e7d0855904812bcb9dea5c43495c7
Source dataset
uspto-grants-1995_03
Patent number
US05395815

Reaction notes

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