Methyl chloroformate → 466-97-7

HRID 1822625Notes

Reaction equation

HRID 1822625 reaction equation
[CH:1]1[C:17]2[CH2:16][C@H:15]3[N:18]([CH2:20][CH2:21][C@@:7]45[C@H:14]3[CH:13]=[CH:12][C@H:10]([OH:11])[C@@H:8]4[O:9][C:5]([C:6]=25)=[C:3]([OH:4])[CH:2]=1)C.COC(Cl)=O.C(=O)([O-])O.[Na+].O.NN>C(Cl)(Cl)Cl>[CH:1]1[C:17]2[CH2:16][C@H:15]3[NH:18][CH2:20][CH2:21][C@:7]45[C@H:8]([C@@H:10]([OH:11])[CH:12]=[CH:13][C@@H:14]34)[O:9][C:5]([C:6]=25)=[C:3]([OH:4])[CH:2]=1

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 24654Hydrazine hydrate (1:1)3×HCID 516892Sodium BicarbonateHCID 5288826Morphine

Product 1

HCID 5462508466-97-7Yield 77.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

After melting 3.82 g of morphine in 190 ml of Chloroform, 20.9 g of methylchloroformate and 16.0 g of sodium hydrogencarbonate are added; then the thus obtained mixture is refluxed for 8 hours. Non-organic material is filtered from the reacted material; the filtered material is subjected to a dehydration with the aid of anhydrous sodium sulfate; and a solvent medium is evaporated under a reduced pressure to obtain a residue thereof having a light yellow color and a viscosity. Into the thus obtained residue, 11.4 ml of 97% hydrazine hydrate is added, and then 15.2 ml of 64% hydrazine hydrate is further added; then the residue with the hydrazine hydrate is refluxed for 12 hours to deposit crystal. The thus deposited crystal is washed with water, acetone and chloroform to obtain 2.81 g of normorphine. Whether the thus obtained substance is a desired normorphine is checked by a nuclear magnetic resonance (NMR) method.

Workup

  1. additionare added
  2. temperaturethen the thus obtained mixture is refluxed for 8 hours
  3. filtrationNon-organic material is filtered from the reacted material
  4. customand a solvent medium is evaporated under a reduced pressure
  5. customto obtain a residue
  6. washThe thus deposited crystal is washed with water, acetone and chloroform

Sources & evidence

ORD record
ord-b5968dc05e47459da54c9a234569c9fe
Source dataset
uspto-grants-2006_05
Patent number
US07037727B1

Reaction notes

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