Chloroform → HCID 15027935, compound

HRID 1729174Notes

Reaction equation

HRID 1729174 reaction equation
C[O:2][C:3]1[CH:30]=[CH:29][C:6]2[NH:7][C:8](=[O:28])[CH:9]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][N:18]([C:21]4[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][N:22]=4)[CH2:17][CH2:16]3)[S:10][C:5]=2[CH:4]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+].C(Cl)(Cl)Cl>C(Cl)Cl>[OH:2][C:3]1[CH:30]=[CH:29][C:6]2[NH:7][C:8](=[O:28])[CH:9]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][N:18]([C:21]4[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][N:22]=4)[CH2:17][CH2:16]3)[S:10][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 15027948HCID 15027948, compound

Product 1

HCID 15027935HCID 15027935, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

360 mg of 7-methoxy-2-{4-[4-(4-methylpyridin-2-yl)-piperazin-1-yl]-butyl}-2H-1,4-benzothiazine-3(4H)-one (see Example 19) prepared analogously to Example 1 were added to 5 ml of dichloromethane with exclusion of moisture. After cooling to -5° C., a solution of 0.73 g of boron tribromide in 1 ml of methylene chloride was added dropwise with stirring. Stirring was then continued for a further 30 minutes at room temperature. The reaction mixture was worked up by adding it with stirring to a mixture of ice and aqueous sodium hydrogen carbonate solution. 200 ml of chloroform were then added. The resulting organic solution was washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The title compound was obtained from the remaining residue by fractional column chromatography. The fractions containing the title compound were concentrated and treated with ether. 30 mg of 7-hydroxy-2-{4-[4-(4-methylpyridin-2-yl)-piperazin-1-yl]butyl}-2H-1,4-benzothiazine-3(4H)-one were obtained as white crystals having a melting point of 212° C.

Workup

  1. stirringStirring
  2. additionby adding it
  3. washThe resulting organic solution was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d750b947d3eb4b6e909c3deceb37b51a
Source dataset
uspto-grants-1994_07
Patent number
US05332733

Reaction notes

Loading…