1,2-Dibromoethane → HCID 13577521, compound

HRID 653009Notes

Reaction equation

HRID 653009 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([S:10][CH2:11][CH3:12])=S)[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:14][OH:15].C(N(CC)CC)C.BrCCBr>O.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:10][CH2:11][CH2:12][O:15][N:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 78391,2-DibromoethaneHCID 8471Triethylamine2×HCID 443297Hydroxyamine hydrochlorideHCID 53698076HCID 53698076, compound

Product 1

HCID 13577521HCID 13577521, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 3-chlorobenzenecarbodithioate (106 g, 0.5 mol) and ethanol (400 ml) was treated with finely powdered hydroxylamine hydrochloride (36 g, 0.5 mol, 97%) with stirring, triethylamine (50.5 g, 70 ml, 0.5 mol) was added dropwise. A slight exotherm was observed. After the addition, the reaction was stirred for 11/2 hours. Ethyl mercaptan was removed using a scrubber and vacuum trap. 1,2-Dibromoethane (95 g, 0.5 mol) was added to the reaction and with stirring, triethylamine (101 g, 140 ml, 1 mol) added dropwise. The initial red colour was completely discharged. When the addition was complete, the reaction was refluxed for 1 hour, cooled to room temperature and the solvent removed to leave a solid. Water was added, the product extracted into ether which was subsequently washed successively with water, 5% potassium hydroxide, water and then dried over anhydrous magnesium sulphate. After evaporation, a white solid remained, 3-(3-chlorophenyl)-5,6-dihydro-1,4,2-oxathiazine, mp 65° C.

Workup

  1. additionAfter the addition
  2. stirringthe reaction was stirred for 11/2 hours
  3. customEthyl mercaptan was removed
  4. stirringwith stirring
  5. additionWhen the addition
  6. temperaturethe reaction was refluxed for 1 hour
  7. customthe solvent removed
  8. customto leave a solid
  9. extractionthe product extracted into ether which
  10. washwas subsequently washed successively with water, 5% potassium hydroxide, water
  11. dry with materialdried over anhydrous magnesium sulphate
  12. customAfter evaporation

Sources & evidence

ORD record
ord-e5b421c4fffd44469eaaf624ffd0d595
Source dataset
uspto-grants-1987_06
Patent number
US04675044

Reaction notes

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