Dimethylformamide → HCID 86731037, compound

HRID 714560Notes

Reaction equation

HRID 714560 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=1.CN(C=O)C.[OH-].[K+].[CH2:26]([CH:28]1[O:30][CH2:29]1)Br>[Cl-].[Na+].O>[O:30]1[CH2:29][CH:28]1[CH2:26][N:6]1[C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:17])[F:18])[CH:16]=[CH:15][C:14]=2[S:13][C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 708210H-Phenothiazine, 2-(trifluoromethyl)-HCID 14797Potassium HydroxideHCID 18430Epibromohydrin

Product 1

HCID 86731037HCID 86731037, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-(trifluoromethyl)-10H-phenothiazine (5.0 g, 18.8 mmol) and DMF (15 mL) at RT was added finely powdered KOH (2.1 g, 37.5 mmol) and (±)-epibromohydrin (3.9 mL, 48.9 mmol). The reaction mixture was stirred at RT for 48 h. Once no starting material was observed by analytical LCMS, EtOAC (250 mL) and brine (250 mL) were added. The organic layer was separated, and the aqueous layer was washed with EtOAC (3×100 mL). The combined organic extracts were washed with brine (2×100 mL), dried over MgSO4, and concentrated to afford the title compound.

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. washthe aqueous layer was washed with EtOAC (3×100 mL)
  4. washThe combined organic extracts were washed with brine (2×100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cd550bba0d82477dba998473435bb7a7
Source dataset
uspto-grants-2015_11
Patent number
US09187439B2

Reaction notes

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