Bromine → HCID 19096814, compound

HRID 893214Notes

Reaction equation

HRID 893214 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10](=S(C)(C)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.[Br:21]Br>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[CH:10]([Br:21])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 86745931HCID 86745931, compound

Product 1

HCID 19096814HCID 19096814, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 2.73 grams (0.01 mole) of ethyl 3-[(4-chlorophenyl)amino]-2-(dimethyloxosulfuranylidene)-3-oxopropanoate prepared in Example XLVII (Compound 205) in 35 milliliters of chloroform was added a solution of 1.37 grams (0.01 mole) of bromine in 35 milliliters of chloroform, dropwise, at ambient temperature. The mixture became dark orange and showed a slight exothermic effect during the feed period. Stirring was continued for 20 minutes, at which time the solution was a clear light yellow in color. It was then evaporated free of solvent and stored at 5° C. for a period of about 64 hours causing the residue to crystallize. Two recrystallizations from hexane-ethyl acetate (10:1) gave 0.58 gram (0.002 mole) of ethyl 3-[(4-chlorophenyl)amino]-2-bromo-3-oxopropanoate having a melting point of 117° C.-119° C.

Workup

  1. customat ambient temperature
  2. customIt was then evaporated free of solvent
  3. waitstored at 5° C. for a period of about 64 hours
  4. customto crystallize
  5. customTwo recrystallizations from hexane-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-0fb73bc271ff4c87b364cf373e654bc8
Source dataset
uspto-grants-1992_06
Patent number
US05123951

Reaction notes

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