Bromine → Hydrogen Bromide

HRID 1954453Notes

Reaction equation

HRID 1954453 reaction equation
[CH:1]1([S:7][C:8](=[S:14])[NH:9][CH2:10][C:11]([Cl:13])=[CH2:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:15]Br>C(#N)C>[BrH:15].[Br:15][CH2:12][C:11]1([Cl:13])[S:14][C:8]([S:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[N:9][CH2:10]1.[BrH:15]

Participants

5

Reactant 2

HCID 24408BromineHCID 53719602HCID 53719602, compound

Product 2

HCID 260Hydrogen BromideHCID 23450657HCID 23450657, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0.5 °C

Procedure

Under a slight stream of nitrogen, 19.0 g of (2-chloro-allyl)-dithiocarbamic acid cyclohexyl ester are placed in 100 ml of acetonitrile and cooled to 0-1° C. Before and during the addition of bromine, the apparatus is flushed thoroughly with nitrogen. Then 14.0 g of bromine are added in the course of 70 minutes in such a manner that the temperature can be maintained at 0-10° C. When the addition is complete, stirring is carried out for about 20 minutes. The reaction mixture is concentrated in vacuo at 20-25° C. 50 ml of hexane are added to the crude product, and the product is filtered off with suction at 20-25° C., washed twice with 45 ml of hexane and dried in vacuo at room temperature. The title product is obtained in the form of the hydrobromide (compound 2.3).

Workup

  1. customthe apparatus is flushed thoroughly with nitrogen
  2. additionThen 14.0 g of bromine are added in the course of 70 minutes in such a manner that the temperature
  3. temperaturecan be maintained at 0-10° C
  4. additionWhen the addition
  5. concentrationThe reaction mixture is concentrated in vacuo at 20-25° C
  6. addition50 ml of hexane are added to the crude product
  7. filtrationthe product is filtered off with suction at 20-25° C.
  8. washwashed twice with 45 ml of hexane
  9. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-876595c08bfb40e09954a3244cf4f61a
Source dataset
uspto-grants-2000_09
Patent number
US06121455

Reaction notes

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