Potassium Carbonate → HCID 57656306, compound

HRID 911413Notes

Reaction equation

HRID 911413 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[OH:19].C([O-])([O-])=O.[K+].[K+].[CH3:26][N:27]([CH3:31])[C:28](Cl)=[S:29]>CC(C)=O.O.CN(C)C(Cl)=S>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:13])[F:14])[CH2:9][CH2:10][C:4]=2[C:3]=1[O:19][C:28](=[S:29])[N:27]([CH3:31])[CH3:26]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27871Dimethylthiocarbamoyl chloride2×HCID 58757109HCID 58757109, compound

Product 1

HCID 57656306HCID 57656306, compoundYield 91.1%

Reagents, catalysts & solvents 3

HCID 27871Dimethylthiocarbamoyl chlorideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent3×

Procedure

Place 7-chloro-6-hydroxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (64.3 g, 219 mmol) in acetone (450 mL) and water (200 mL) with K2CO3 (91.8 g, 664 mmol) and dimethylthiocarbamoyl chloride (31.5 g, 255 mmol). Stir at ambient temperature for 1.25 h. Add additional dimethylthiocarbamoyl chloride (3 g, 24 mmol) and stir for an additional 1.75 h at ambient temperature. Add more dimethylthiocarbamoyl chloride (0.7 g, 5.7 mmol) and water (150 mL) to the mixture and stir for 0.5 h at ambient temperature. Slowly add water (500 mL) to the reaction over 2 h to promote crystallization and stir the resulting slurry at ambient temperature for 1.5 h. Collect the solid by filtration to give the desired intermediate (76 g, 91%).

Workup

  1. stirringstir for an additional 1.75 h at ambient temperature
  2. stirringstir for 0.5 h at ambient temperature
  3. customcrystallization
  4. stirringstir the resulting slurry at ambient temperature for 1.5 h
  5. customCollect the solid
  6. filtrationby filtration

Sources & evidence

ORD record
ord-e316f7f91b9741ea9ad9b40d59e3a38f
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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