Chloral Hydrate → HCID 10944680, compound

HRID 2282556Notes

Reaction equation

HRID 2282556 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[Cl:9][C:10]([Cl:15])([Cl:14])[CH:11](O)O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[Cl:9][C:10]([Cl:15])([Cl:14])[C@@H:11]1[N:1]2[CH2:8][CH2:7][CH2:6][C@H:2]2[C:3](=[O:5])[O:4]1

Participants

5

Reactant 3

HCID 2707Chloral HydrateHCID 24436Sodium SulfateHCID 145742L-Proline

Product 1

HCID 10944680HCID 10944680, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of L-proline (10.0 g, 87.0 mmol) and chloral hydrate (21.6 g, 130 mmol) in chloroform (100 mL) was heated at reflux for 6 h under a soxlet adapter charged with sodium sulfate. The cooled mixture was washed with water (2×), dried (MgSO4) and concentrated in vacuo. The product was recrystallised from boiling absolute ethanol to give the title compound as white needles (13.3 g, 63%). 1H NMR (400 MHz, CDCl3): 1.65-1.83 (1H, m), 1.86-2.01 (1H, m), 2.04-2.31 (2H, m), 3.06-3.18 (1H, m), 3.36-3.49 (1H, m), 4.12 (1H, dd, J 4.6, 4.0), 5.16 (1H, s).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h under a soxlet adapter
  3. washThe cooled mixture was washed with water (2×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe product was recrystallised

Sources & evidence

ORD record
ord-10f663c11a724dd0a98ed11fb6ee99ca
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

Loading…