Ethyl chloroformate → HCID 20556839, compound

HRID 1660505Notes

Reaction equation

HRID 1660505 reaction equation
[C:1]1([C:7]2[N:12](C)[CH2:11][CH:10]([N:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15]3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:24]([O:26][C:27](Cl)=[O:28])[CH3:25].[C:30](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]1([C:7]2[N:12]([C:27]([O:26][CH2:24][CH3:25])=[O:28])[CH:11]([CH3:30])[CH:10]([N:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15]3)[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 20556841HCID 20556841, compound

Product 1

HCID 20556839HCID 20556839, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 3.08 g. of 3-phenyl-6-(1,2,3,4-tetrahydro-2-isoquinolyl)-methyl-5,6-dihydro-4H-1,2,4-oxadiazine 50 ml. of absolute acetone, 1.0 ml. of chlorocarbonic acid ethyl ester and 1.0 g. of anhydrous potassium carbonate are added. The reaction mixture is refluxed for 6 hours. The insoluble substances are filtered off while hot and the solvent is evaporated. After recrystallization of the residue from cyclohexane 1.18 g. of 3-phenyl-4-ethoxycarbonyl-6-(1,2,3,4-tetrahydro-2-isoquinolyl)-methyl-5,6-dihydro-1,2,4-oxadiazine are obtained, melting at 114° to 116° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 6 hours
  2. filtrationThe insoluble substances are filtered off while hot and the solvent
  3. customis evaporated
  4. customAfter recrystallization of the residue from cyclohexane 1.18 g

Sources & evidence

ORD record
ord-5da915989dae4cae9de9090c5dbb715b
Source dataset
uspto-grants-1981_12
Patent number
US04308270

Reaction notes

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