Ethyl chloroformate → HCID 146095, compound

HRID 485830Notes

Reaction equation

HRID 485830 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][N:9]([CH3:12])[CH2:8][CH:7]2[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1.Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1C=CC=CC=1>[CH2:24]([O:23][C:21]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][N:9]([CH3:12])[CH2:8][CH:7]2[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)=[O:22])[CH3:25]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 14493695HCID 14493695, compound

Product 1

HCID 146095HCID 146095, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 13.1 g (0.047 mole) of 8-amino-4-p-chloro-phenyl-2-methyl-1,2,3,4-tetrahydro-isoquinoline and 300 ml of anhydrous benzene is admixed with a solution of 6.8 g (0.0625 mole, 6 ml) of ethyl chloroformate and 60 ml of anhydrous benzene. The reaction mixture is refluxed for 2.5 hours and the benzene is distilled off in vacuo. The residue is dissolved in 10 ml of water, made alkaline with 10 ml of a concentrated ammonium hydroxide solution and extracted three times with 100 ml of chloroform each. The chloroform extracts are united, dried over anhydrous sodium sulfate, evaporated and the residue is recrystallized twice from ethanol. Thus 7.3 g of the title compound are obtained in the form of white crystals, yield 45.6%, Mp.: 155° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 2.5 hours
  2. distillationthe benzene is distilled off in vacuo
  3. dissolutionThe residue is dissolved in 10 ml of water
  4. extractionextracted three times with 100 ml of chloroform each
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customthe residue is recrystallized twice from ethanol

Sources & evidence

ORD record
ord-39b05fb0af554dcf8864f430c6417dcb
Source dataset
uspto-grants-1985_08
Patent number
US04537895

Reaction notes

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