Potassium Carbonate → HCID 57656333, compound

HRID 2041299Notes

Reaction equation

HRID 2041299 reaction equation
[OH:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:19].C(=O)([O-])[O-].[K+].[K+].[CH3:26][N:27]([CH3:31])[C:28](Cl)=[S:29]>CC(C)=O>[CH3:26][N:27]([CH3:31])[C:28]([O:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13](=[O:18])[C:14]([F:17])([F:15])[F:16])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:19])=[S:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27871Dimethylthiocarbamoyl chlorideHCID 57656558HCID 57656558, compound

Product 1

HCID 57656333HCID 57656333, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dissolve 6-hydroxy-7-methyl-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.0 g, 3.66 mmol) in acetone (50 mL). Add potassium carbonate (1.517 g, 10.98 mmol) and dimethylthiocarbamoyl chloride (0.904 g, 7.32 mmol). Heat the mixture at reflux overnight. Remove the solvent in vacuo and partition the residue between water and DCM. Dry the organic phase over Na2SO4, filter and concentrate. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1) to obtain the desired intermediate as a solid (1.18 g, 90%). MS (ES+) m/z: 361 (M+H)+.

Workup

  1. temperatureHeat the mixture
  2. temperatureat reflux overnight
  3. customRemove the solvent in vacuo
  4. custompartition the residue between water and DCM
  5. dry with materialDry the organic phase over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 9:1)

Sources & evidence

ORD record
ord-4d5944fb4ddc413aa36ed32133a8c727
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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