Bromine → HCID 14122311, compound

HRID 477582Notes

Reaction equation

HRID 477582 reaction equation
BrBr.[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:16]#[N:17])[C:13]([NH2:15])=[S:14])=[CH:8][CH:7]=1)([O-:5])=[O:4].C(=O)([O-])O.[Na+]>ClC(Cl)C.ClCCCl>[NH2:15][C:13]1[S:14][C:10]2[CH:11]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=[CH:8][C:9]=2[C:12]=1[C:16]#[N:17]

Participants

6

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 14122310HCID 14122310, compound

Product 1

HCID 14122311HCID 14122311, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 1.3 ml (25 mmol) of bromine in 10 ml of dichloroethane is added dropwise to a suspension of 5.53 g (25 mmol) of p-nitrophenylcyanothioacetamide and 4.2 g (50 mmol) of sodium hydrogencarbonate in 40 ml of 1,2-dichloroethane. The temperature is maintained at 20° C. by cooling with ice-water. This is followed by 30 minutes of stirring, filtering off with suction and washing with water. Drying in vacuo at 50° C. leaves 4.9 g of a brown powder=89% of theory.

Workup

  1. filtrationfiltering off with suction
  2. washwashing with water
  3. customDrying in vacuo at 50° C.

Sources & evidence

ORD record
ord-684eb2c1aded419e89095d233d38ebcf
Source dataset
uspto-grants-1989_12
Patent number
US04888432

Reaction notes

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