Dimethylformamide → HCID 53789916, compound

HRID 1608549Notes

Reaction equation

HRID 1608549 reaction equation
[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11]([OH:13])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].CN(C)C=O.S(Cl)(Cl)=O.[CH2:25]([NH2:43])[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][CH2:40][CH2:41][CH3:42]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:25]([NH:43][C:11](=[O:13])[CH:10]=[CH:9][C:8]1[CH:7]=[CH:6][C:5]([O:4][C:1](=[O:3])[CH3:2])=[CH:15][CH:14]=1)[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][CH2:40][CH2:41][CH3:42]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 15793OctadecylamineHCID 24386Thionyl ChlorideHCID 85857Cinnamic acid, p-hydroxy-, acetate

Product 1

HCID 53789916HCID 53789916, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

Under a nitrogen atmosphere, 4-acetoxycinnamic acid (150 g) and N,N-dimethylformamide (5 ml) were suspended in chloroform (800 ml) and thereto was added dropwise thionyl chloride (104 g) over a period of about 30 minutes. After completion of the addition, the reaction mixture was reflexed with heating for 1 hour to prepare the corresponding acid chloride. The reaction mixture was cooled to room temperature and thereto was added dropwise a solution of octadecylamine (196 g) and triethylamine (81 g) in chloroform (50 ml) over a period of about 30 minutes, followed by refluxing with heating for 3 hours. The reaction mixture was cooled to room temperature to precipitate a white crystal, which was filtered off under reduced pressure and dried to obtain N-octadecyl-p-acetoxycinnamamide (258 g). Yield 78%. This was suspended in 1,4-dioxane (1200 ml) and thereto was added aqueous KOH solution 50%; 127 g) and the reaction was allowed to proceed at 40°-45° C. for 24 hours. After completion of the reaction, the reaction mixture was cooled to room temperature to precipitate a white crystal, which was filtered off under reduced pressure. This crystal was washed with distilled water and recrystallized from methanol to obtain the desired product (211 g). Yield 90%; m.p. 114° C.

Workup

  1. additionAfter completion of the addition
  2. temperaturewith heating for 1 hour
  3. temperatureby refluxing
  4. temperaturewith heating for 3 hours
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customto precipitate a white crystal, which
  7. filtrationwas filtered off under reduced pressure
  8. customdried

Sources & evidence

ORD record
ord-ebae5944d4514dcc8cff4dc664439ce1
Source dataset
uspto-grants-1995_03
Patent number
US05395815

Reaction notes

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