Decanoyl chloride → HCID 54192954, compound

HRID 648881Notes

Reaction equation

HRID 648881 reaction equation
[CH:1]1[CH:6]=[C:5]([CH:7]([OH:16])[C:8]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])[N:4]=[CH:3][CH:2]=1.[C:17](Cl)(=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>>[C:17]([O:9][C:8]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][N:15]=1)=[C:7]([O:16][C:17](=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:5]1[CH:6]=[CH:1][CH:2]=[CH:3][N:4]=1)(=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

3

Reactant 2

HCID 66982Decanoyl chlorideHCID 95624α-Pyridoin

Product 1

HCID 54192954HCID 54192954, compoundYield 9.9%

Procedure

To 21.0 g (0.1 mole) of pulverized α-pyridoin (commercially available, e.g. from Aldrich Chemical Co.) was added 9.5 g (0.05 mole) decanoyl chloride. The reaction mixture was mixed for 30 minutes, after which it became solid. The solid was extracted with acetonitrile and the acetonitrile solution evaporated to yield an oily semisolid. Recrystallization from 70% cyclohexanone-30% acetone yielded 1.3 g (9.9%) white fine needles of compound NA-IV, m.p. 89°-90° C.

Workup

  1. additionThe reaction mixture was mixed for 30 minutes
  2. extractionThe solid was extracted with acetonitrile
  3. customthe acetonitrile solution evaporated
  4. customto yield an oily semisolid
  5. customRecrystallization from 70% cyclohexanone-30% acetone

Sources & evidence

ORD record
ord-31f283b9a2074b1da65fd775de3e0cb5
Source dataset
uspto-grants-1988_04
Patent number
US04737439

Reaction notes

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