Dimethylformamide → HCID 18942237, compound

HRID 355424Notes

Reaction equation

HRID 355424 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([N:7]1[C:20]2[CH:19]=[CH:18][C:17]([CH2:21]O)=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:6].CN(C=O)C>C(Cl)Cl>[Cl:3][CH2:21][C:17]1[CH:18]=[CH:19][C:20]2[N:7]([CH2:5][CH3:6])[C:8]3[C:13]([S:14][C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 11357340HCID 11357340, compound

Product 1

HCID 18942237HCID 18942237, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an atmosphere of argon, thionyl chloride (0.65 ml, 8.86 mmol) was added at 0° C. to a mixture of 10-ethyl-3-hydroxymethylphenothiazine (1.14 g, 4.43 mmol), DMF (0.1 ml) and methylene chloride (12 ml), and the mixture was stirred for 1 hour and then at room temperature for 1 hour. The reaction mixture was concentrated under a reduced pressure, and chloroform and a saturated sodium bicarbonate aqueous solution (each 20 ml) were added to the residue in that order. The reaction product was extracted with ethyl acetate, and the extract was washed with saturated sodium chloride aqueous solution. The extract was dried over anhydrous magnesium sulfate, and then concentrated under a reduced pressure to give 3-chloromethyl-10-ethylphenothiazine (1.17 g, 4.24 mmol, 96%) as brown oil.

Workup

  1. waitat room temperature for 1 hour
  2. concentrationThe reaction mixture was concentrated under a reduced pressure, and chloroform
  3. additiona saturated sodium bicarbonate aqueous solution (each 20 ml) were added to the residue in that order
  4. extractionThe reaction product was extracted with ethyl acetate
  5. washthe extract was washed with saturated sodium chloride aqueous solution
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-52f9a292bb07469bb9db559e45eed43b
Source dataset
uspto-grants-1998_11
Patent number
US05830902

Reaction notes

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