Bromine → HCID 63991321, compound

HRID 2038381Notes

Reaction equation

HRID 2038381 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]#[N:11])[CH:7]=[CH:8][CH:9]=1)(=O)[CH3:2].BrBr.[NH2:14][C:15](=[S:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>Cl.C(O)(=O)C.CCO>[C:10]([C:6]1[CH:5]=[C:4]([C:1]2[N:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[S:21][CH:2]=2)[CH:9]=[CH:8][CH:7]=1)#[N:11]

Participants

7

Reactant 3

HCID 24408BromineHCID 802223-AcetylbenzonitrileHCID 2733398Ethyl thiooxamate

Product 1

HCID 63991321HCID 63991321, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 176Acetic AcidSolvent2×HCID 702EthanolSolvent2×

Procedure

At room temperature, 10 drops of a conc. aqueous hydrogen chloride solution are added to 5.00 g (34.4 mmol) of 3-acetylbenzenecarbonitrile in 40 ml of conc. acetic acid. 1.8 ml (34.4 mmol) of bromine in 10 ml of conc. acetic acid are subsequently added dropwise over a period of 1 h, and after the end of the addition, the reaction mixture is poured onto ice. After extraction of the aqueous phase with dichloromethane, the combined organic phases are dried over MgSO4, filtered and concentrated under reduced pressure. The solid obtained (8.00 g) is provided in 250 ml of EtOH and heated under reflux, a solution of 3.77 g (28.3 mmol) of ethyl amino(thioxo)acetate in 50 ml of ethanol is added dropwise and the mixture is stirred under reflux for 3 h. The reaction solution is cooled and the precipitate formed is collected by filtration. The mother liquor is concentrated under reduced pressure, the residue is taken up in a little ethanol and the solid formed is subsequently collected by filtration. 5.75 g (65% of theory) of the title compound are obtained after combining the solids.

Workup

  1. additionafter the end of the addition
  2. additionthe reaction mixture is poured onto ice
  3. extractionAfter extraction of the aqueous phase with dichloromethane
  4. dry with materialthe combined organic phases are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe solid obtained (8.00 g)
  8. temperatureheated
  9. temperatureunder reflux
  10. temperatureunder reflux for 3 h
  11. temperatureThe reaction solution is cooled
  12. customthe precipitate formed
  13. filtrationis collected by filtration
  14. concentrationThe mother liquor is concentrated under reduced pressure
  15. customthe solid formed
  16. filtrationis subsequently collected by filtration

Sources & evidence

ORD record
ord-2abf5240640b4fb094d9af5649b3f085
Source dataset
uspto-grants-2013_11
Patent number
US08575357B2

Reaction notes

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