2-(methylamino)benzenethiol → HCID 15027933, compound

HRID 1729172Notes

Reaction equation

HRID 1729172 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].C(=O)([O-])O.[Na+].Br[CH:16]([CH2:20][CH2:21][CH2:22][CH2:23][Br:24])[C:17](Br)=[O:18]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.C(Cl)(Cl)Cl>[Br:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:16]1[C:17](=[O:18])[N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[S:9]1

Participants

6

Reactant 3

HCID 4521612-(methylamino)benzenethiolHCID 516892Sodium BicarbonateHCID 15027913HCID 15027913, compound

Product 1

HCID 15027933HCID 15027933, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6212ChloroformSolvent2×

Conditions

Temperature
5 °C

Procedure

4.5 g (=0.032 m) of 2-(methylamino)-thiophenol, 6 g of triethylbenzylammonium chloride, and 11.20 g of sodium hydrogen carbonate were added to 120 ml of chloroform. The resulting suspension was cooled to 5° C., and then a solution of 10.88 g of 2,6-dibromohexanoyl bromide in 20 ml of chloroform was added dropwise so slowly that the temperature did not exceed 5° C. 20 minutes were required for the addition. The reaction mixture was then allowed to warm to room temperature and was subsequently heated under reflux for 4 hours. The reaction mixture was worked up by cooling and filtering it. The chloroform phase was washed, dried over sodium sulfate, and the solvent was distilled off. The 2-(4-bromobutyl)-4-methyl-2H-1,4-benzothiazine-3(4H)-one which formed was isolated from the remaining residue by fractional column chromatography. 2.78 g of white crystals having a melting point of 116° C. were obtained.

Workup

  1. customdid not exceed 5° C
  2. addition20 minutes were required for the addition
  3. temperatureto warm to room temperature
  4. temperaturewas subsequently heated
  5. temperatureunder reflux for 4 hours
  6. temperatureby cooling
  7. filtrationfiltering it
  8. washThe chloroform phase was washed
  9. dry with materialdried over sodium sulfate
  10. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-50aeeaf9ee8b401b9400658386da7065
Source dataset
uspto-grants-1994_07
Patent number
US05332733

Reaction notes

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