1,2-Dichloroethane → 2H-1,4-Benzothiazin-3(4H)-one, 2-butyl-

HRID 1175682Notes

Reaction equation

HRID 1175682 reaction equation
Br[CH:2]([CH2:6][CH2:7][CH2:8][CH3:9])[C:3]([OH:5])=O.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[SH:17].C([O-])([O-])=O.[K+].[K+].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.Cl>[CH2:6]([CH:2]1[S:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][C:3]1=[O:5])[CH2:7][CH2:8][CH3:9]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 87132-AminothiophenolHCID 11430Potassium CarbonateHCID 120132-Bromohexanoic acidHCID 757711-Hydroxybenzotriazole

Product 1

HCID 103985982H-1,4-Benzothiazin-3(4H)-one, 2-butyl-

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromohexanoic acid (10 mmol, 1951 mg) in DMF (10 ml) was added 2-aminothiophenol (10 mmol, 1252 mg) and K2CO3 (50 mmol, 9.9 g) and the reaction mixture stirred at room temperature for 1 h. EDC (10 mmol, 1917 mg) and HOBt (10 mmol, 1351 mg) were added and the reaction mixture was stirred at room temperature for a further 1.5 h. The reaction mixture was diluted with 1N HCl and extracted with ethyl acetate. The organic phase was washed with sat. NaHCO3, brine, dried over Na2SO4 and then filtered through a short plug of silica gel. Evaporation of the solvent gave product as a yellow solid that was used without further purification. LC/MS (10% to 99%): M/Z (M+H)+ (obs)=222.0; tR=3.07.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for a further 1.5 h
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with sat. NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered through a short plug of silica gel
  6. customEvaporation of the solvent
  7. customgave product as a yellow solid that
  8. customwas used without further purification

Sources & evidence

ORD record
ord-7cd744b83fd649de8c55f5e224193438
Source dataset
uspto-grants-2010_11
Patent number
US07842686B2

Reaction notes

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