Tetrahydrofuran → HCID 20143125, compound

HRID 649322Notes

Reaction equation

HRID 649322 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:19]=2[O:26]C2CCCCO2)[C:11](=[O:12])[N:10]([CH3:13])[C:9]2[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=2[S:7]1.O1CCCC1.[CH3:38][SH:39].[Na]>C(O)C>[OH:26][C:19]1[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:18]=1[C:6]1([CH2:5][CH2:4][CH2:3][CH2:2][S:39][CH3:38])[C:11](=[O:12])[N:10]([CH3:13])[C:9]2[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=2[S:7]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 20142998HCID 20142998, compoundHCID 45051789Methylmercaptan sodium

Product 1

HCID 20143125HCID 20143125, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 2-(4-bromobutyl)-2-[5-methoxy-2-(tetrahydropyran-2-yloxy)phenyl]-4-methyl-3-oxo-2H-1,4-benzothiazine (4.9 g, compound No. 34) in ethanol (25 ml), 20-25% aqueous sodium methyl mercaptan solution (16.6 ml) is added. Ethanol (15 ml) and tetrahydrofuran (20 ml) are added to the mixture. The mixture is stirred for 45 minutes at room temperature, and concentrated in vacuo. 2N Hydrochloric acid (50 ml), tetrahydrofuran (25 ml) and ethanol (25 ml) are added to the residue dissolved in tetrahydrofuran (50 ml), and the mixture is stirred for 45 minutes at room temperature. The reaction mixture is poured into a mixture of ethyl acetate and water. The organic layer is washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The separated crystals are collected by filtration to give 3.0 g (77.3%) of the titled compound.

Workup

  1. concentrationconcentrated in vacuo
  2. addition2N Hydrochloric acid (50 ml), tetrahydrofuran (25 ml) and ethanol (25 ml) are added to the residue
  3. dissolutiondissolved in tetrahydrofuran (50 ml)
  4. stirringthe mixture is stirred for 45 minutes at room temperature
  5. additionThe reaction mixture is poured into a mixture of ethyl acetate and water
  6. washThe organic layer is washed with saturated aqueous sodium bicarbonate solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. filtrationThe separated crystals are collected by filtration

Sources & evidence

ORD record
ord-bb5153ef7ecb49eb8a1810454f2a4986
Source dataset
uspto-grants-1988_04
Patent number
US04739050

Reaction notes

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