Hydrazine hydrate (1:1) → HCID 21260121, compound

HRID 398755Notes

Reaction equation

HRID 398755 reaction equation
[CH2:1]([S:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=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][CH3:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[NH2:44][NH2:45]>C(O)CC>[CH2:1]([S:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([NH:44][NH2:45])=[O:30])[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][CH3:16]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 521998p-Toluenesulfonic acid monohydrateHCID 21259933HCID 21259933, compound

Product 1

HCID 21260121HCID 21260121, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

22.1 Grams of 11-(hexadecylthio)undecanoic 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. Thereafter, to the solution was added 12.5 g of hydrazine monohydrate, followed by refluxing with heating for further 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 16.0 g of the desired product. m.p. 108° C.

Workup

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

Sources & evidence

ORD record
ord-5948c1ebb8704748b16b136d4ea16f37
Source dataset
uspto-grants-1998_10
Patent number
US05817599

Reaction notes

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