Methyl chloroformate → HCID 13067117, compound

HRID 647626Notes

Reaction equation

HRID 647626 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[C:6]3[C:7](=[CH:18][NH:19][CH:20]=3)[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.CC(C)([O-])C.[K+].Cl[C:30]([O:32][CH3:33])=[O:31]>CN(C)C=O.O>[CH3:33][O:32][C:30]([N:19]1[CH:20]=[C:6]2[C:7]([CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]3[CH:3]=[C:2]([Cl:1])[CH:22]=[CH:21][C:5]=32)=[CH:18]1)=[O:31]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 23665647Potassium tert-butoxideHCID 135967503HCID 135967503, compound

Product 1

HCID 13067117HCID 13067117, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In one portion 6.0 g (18.3 mmol) of 8-chloro-6-(2-chlorophenyl)-2H,4H-pyrrolo[3,4-d][2]benzazepine was added to a solution of 3.0 g (26.5 mmol) of potassium t-butoxide in 50 ml of dimethylformamide which was cooled to 0°. When solution was complete 1.8 ml (2.3 g; 24.5 mmol) of methyl chloroformate was added and the resulting mixture was stirred for 15 min. The mixture was diluted with 150 ml of water and the resulting precipitate was collected by filtration. The precipitate was dissolved in methylene chloride and washed with water. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure. The residue crystallized from ether to give an off-white solid. Recrystallization from a mixture of methylene chloride and ether gave off-white fine needles, mp 185°-186° (dec.).

Workup

  1. temperaturewas cooled to 0°
  2. additionwas added
  3. filtrationthe resulting precipitate was collected by filtration
  4. dissolutionThe precipitate was dissolved in methylene chloride
  5. washwashed with water
  6. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  7. concentrationconcentrated at reduced pressure
  8. customThe residue crystallized from ether
  9. customto give an off-white solid
  10. customRecrystallization
  11. additionfrom a mixture of methylene chloride and ether
  12. customgave off-white fine needles, mp 185°-186° (dec.)

Sources & evidence

ORD record
ord-e9bb97d2b5fe4588b773a73f1d83ff30
Source dataset
uspto-grants-1983_10
Patent number
US04409390

Reaction notes

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