Hydrochloric Acid → HCID 53789174, compound

HRID 893094Notes

Reaction equation

HRID 893094 reaction equation
[Br:1][C:2](=[CH2:19])[CH2:3][CH2:4][C:5]([NH:7][CH:8](C(OCC)=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:6].[Cl-].[Na+].Cl>CN(C)C=O.O.O1CCOCC1>[Br:1][C:2](=[CH2:19])[CH2:3][CH2:4][C:5]([NH:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:6]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 53941200Diethyl (2-Bromoallyl)acetamidomalonate

Product 1

HCID 53789174HCID 53789174, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 312751,4-DioxaneCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of Example 3H (3.36 g, 10.0 mmol) in dimethylformamide (10 mL) was added sodium chloride (586 mg, 10.0 mmol), water (360 microliters, 20 mmol) and 4N hydrochloride acid in dioxane (0.012 mL, 0.5 mmol). The reaction vessel was Firestone purged three times and placed under a positive nitrogen pressure. The reaction mixture was heated at reflux for 24 hours and then concentrated in vacuo. The residue obtained was diluted with water (5 mL) and extracted with ether (3×15 mL). The combined organic extracts were decolorized with charcoal (0.5 g), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the title product (2.51 g, 95%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) 1.29 (t, 3H), 2.04 (s, 3H), 2.99 (m, 2H), 4.22 (q, 2H), 4.79 (m, 1H), 5.53 (d, 1H), 5.68 (m, 1H), 6.44 (d, 1H); IR (film) 1195, 1220, 1370, 1540, 1660, 1740, 2990, 3050, and 3300 cm-1. MS (DCI/NH3) m/e 264/266 (M+H)+, 281/283 (M+H+NH3)+. Anal. Calcd. for C9H14NO3Br: C, 40.92; H, 5.34; N, 5.30. Found: C, 42.04; N, 5.48; N, 5.26.

Workup

  1. custompurged three times
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 24 hours
  4. concentrationconcentrated in vacuo
  5. customThe residue obtained
  6. extractionextracted with ether (3×15 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63940bd9174d48c6a5f6f87af50fac9e
Source dataset
uspto-grants-1992_06
Patent number
US05122514

Reaction notes

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