Dimethylformamide → 10-(3-Chloropropyl)-2-(trifluoromethyl)-10H-phenothiazine

HRID 714563Notes

Reaction equation

HRID 714563 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.Br[CH2:25][CH2:26][CH2:27][Cl:28]>[Cl-].[Na+].O>[Cl:28][CH2:27][CH2:26][CH2:25][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

5

Reactant 3

HCID 6228DimethylformamideHCID 708210H-Phenothiazine, 2-(trifluoromethyl)-HCID 80061-Bromo-3-chloropropane

Product 1

HCID 7429410-(3-Chloropropyl)-2-(trifluoromethyl)-10H-phenothiazine

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 2-(trifluoromethyl)-10H-phenothiazine (2.04 g, 7.6 mmol) and DMF (16 mL) was mixed with CS2CO3 (7.5 g, 22.9 mmol) and 1-bromo-3-chloropropane (1.1 mL, 11.5 mmol) The reaction mixture was heated at 65° C. for 12 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-8c25cd43d1e34ec78d97cf17fa94fe52
Source dataset
uspto-grants-2015_11
Patent number
US09187439B2

Reaction notes

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