1,2-Dibromoethane → HCID 13577542, compound

HRID 653007Notes

Reaction equation

HRID 653007 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([C:9]([S:11][CH2:12][CH3:13])=S)[CH:6]=[CH:7][CH:8]=1.Cl.[NH2:17][OH:18].C(N(CC)CC)C.BrCCBr>C(O)C.O>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([C:9]2[S:11][CH2:12][CH2:13][O:18][N:17]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 78391,2-DibromoethaneHCID 8471Triethylamine2×HCID 443297Hydroxyamine hydrochlorideHCID 53806070HCID 53806070, compound

Product 1

HCID 13577542HCID 13577542, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 962WaterSolvent

Procedure

Ethyl 3-(trifluoromethyl)benzenecarbodithioate (24.7 g, 0.1 mol) was dissolved in ethanol (50 ml) in which was suspended hydroxylamine hydrochloride (7 g, 0.1 mol). With stirring, triethylamine (10.1 g, 0.1 mol) in ethanol (25 ml) was added dropwise. After 5 hours, ethyl mercaptan was removed under reduced pressure through a KOH scrubber. 1,2-Dibromoethane (19 g, 0.1 mol) was added to the reaction mixture followed by dropwise addition of triethylamine (30 ml) in ethanol (50 ml). A white precipitate formed. After the addition was complete, the reaction mixture was warmed until it was homogenous, then left at room temperature overnight. Water was added, the product extracted into ether, the ether solution washed with dilute sodium hydroxide (2N approx.), then water, dried over anhydrous magnesium sulphate and evaporated to leave an oil which was distilled to give 5,6-dihydro-3-[3-(trifluoromethyl)phenyl]-1,4,2-oxathiazine, bp 113°/0.2 mm.

Workup

  1. customethyl mercaptan was removed under reduced pressure through a KOH scrubber
  2. customA white precipitate formed
  3. additionAfter the addition
  4. temperaturethe reaction mixture was warmed until it
  5. waitleft at room temperature overnight
  6. extractionthe product extracted into ether
  7. washthe ether solution washed with dilute sodium hydroxide (2N approx.)
  8. dry with materialwater, dried over anhydrous magnesium sulphate
  9. customevaporated
  10. customto leave an oil which
  11. distillationwas distilled

Sources & evidence

ORD record
ord-fac3427d83a9450c9da35bf8899f1568
Source dataset
uspto-grants-1987_06
Patent number
US04675044

Reaction notes

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