HCID 10591743, compound → HCID 178470821, compound

HRID 2286271Notes

Reaction equation

HRID 2286271 reaction equation
Br[CH:2]([C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:18](=[S:21])([S-:20])[NH2:19].[NH4+]>C(O)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]2[N:19]=[C:18]([SH:21])[S:20][C:2]=2[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 10591743HCID 10591743, compoundHCID 11083854Ammonium dithiocarbamate

Product 1

HCID 178470821HCID 178470821, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

50.0 g. (0.157 m.) 3-bromo-3-p-chlorobenzoylpropionic acid, ethyl ester and 17.5 g. (0.157 m.) ammonium dithiocarbamate in 500 ml. absolute ethanol are heated at gentle reflux for 5 hours. The reaction mixture is allowed to stand at room temperature overnight. The solid which results is dissolved in 800 ml. of methylene chloride and the solution is washed with 500 ml. of water. The methylene chloride layer is dried over anhydrous magnesium sulfate, and after removal of the methylene chloride the residual solid is recrystallized from ethanol. 39.2 g. (80% yield) of title product is obtained, m.p. 176°-178° C.

Workup

  1. temperatureat gentle reflux for 5 hours
  2. customThe solid which results
  3. dissolutionis dissolved in 800 ml
  4. washof methylene chloride and the solution is washed with 500 ml
  5. dry with materialThe methylene chloride layer is dried over anhydrous magnesium sulfate
  6. customafter removal of the methylene chloride the residual solid
  7. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-41f2dd002bf449f8bb7118aefdce3965
Source dataset
uspto-grants-1982_04
Patent number
US04327221

Reaction notes

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