Chloral → HCID 370682, compound

HRID 1912436Notes

Reaction equation

HRID 1912436 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4].O=[CH:10][C:11]([Cl:14])([Cl:13])[Cl:12]>C(#N)C>[Cl:12][C:11]([Cl:14])([Cl:13])[CH:10]1[N:1]2[CH2:8][CH2:7][CH2:6][CH:2]2[C:3](=[O:5])[O:4]1

Participants

4

Reactant 2

HCID 6407ChloralHCID 8988D-Proline

Product 1

HCID 370682HCID 370682, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of D-proline (100.0 g) in acetonitrile (400 ml) was added dropwise chloral (169 ml) at room temperature, and the mixture was stirred for 18 hours. The mixture was filtered, and the filtrate was concentrated under reduced pressure. To the resulting residue was added water, and the mixture was extracted with chloroform. The separated organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was slurry-washed with n-hexane/ethyl acetate (20/1, 900 ml) to give the titled compound (159.7 g).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the resulting residue was added water
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe resulting residue was slurry-washed with n-hexane/ethyl acetate (20/1, 900 ml)

Sources & evidence

ORD record
ord-2e282ef52f3f421a85ef9710cda6e1f1
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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