Hydrochloric Acid → HCID 86090158, compound

HRID 2174354Notes

Reaction equation

HRID 2174354 reaction equation
[CH3:1][O:2][C:3](=[O:20])[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]Br.[CH2:21]([C:24]#[N:25])[C:22]#[N:23].C([O-])([O-])=O.[K+].[K+].Cl>CC#N.O>[CH3:1][O:2][C:3](=[O:20])[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][CH:21]([C:24]#[N:25])[C:22]#[N:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 11430Potassium CarbonateHCID 2736822Methyl 16-bromohexadecanoate

Product 1

HCID 86090158HCID 86090158, compoundYield 139.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To 16-bromohexadecanoic acid methyl ester (1.40 g, 4.0 mmol) in MeCN (20 ml) were added malonodinitrile (1.01 g, 15.3 mmol) and K2CO3 (0.92 g, 6.64 mmol). The mixture was stirred at 80° C. for 18.5 h. Water (50 ml) and 1N HCl (50 ml) were added, and the product was extracted with AcOEt. The combined extracts were washed with brine, dried over MgSO4, and concentrated under reduced pressure. 1.87 g (100%) of an oil was obtained which crystallized completely after some hours.

Workup

  1. extractionthe product was extracted with AcOEt
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-47940eab15a64ade9965be2c94f4d99c
Source dataset
uspto-grants-2015_06
Patent number
US09061067B2

Reaction notes

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