Docosanoic Acid → HCID 18183943, compound

HRID 398750Notes

Reaction equation

HRID 398750 reaction equation
[C:1]([OH:24])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[NH2:38][NH2:39]>C(O)CC>[C:1]([NH:38][NH2:39])(=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 8215Docosanoic AcidHCID 24654Hydrazine hydrate (1:1)HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 18183943HCID 18183943, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

17.0 Grams of docosanoic acid, 1.0 g of p-toluenesulfonic acid monohydrate and 200 ml of n-propanol were charged in a flask equipped with a stirrer, a condenser and a calcium chloride drying tube and refluxed with heating for 4 hours. To the resulting solution was added 12.5 g of hydrazine monohydrate, followed by continuing the refluxing with heating for 20 hours. The reaction mixture was cooled to room temperature and the precipitated crystal was filtered off under reduced pressure and washed with distilled water. The crystal was recrystallized from 2-propanol to obtain 14.2 g of the desired product. m.p. 117° C.

Workup

  1. customequipped with a stirrer, a condenser and a calcium chloride drying tube
  2. temperaturerefluxed
  3. temperaturewith heating for 4 hours
  4. temperaturewith heating for 20 hours
  5. filtrationthe precipitated crystal was filtered off under reduced pressure
  6. washwashed with distilled water
  7. customThe crystal was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-b972959af1ae4133b44f951966ab9263
Source dataset
uspto-grants-1998_10
Patent number
US05817599

Reaction notes

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