Chloroform → HCID 13217732, compound

HRID 1973412Notes

Reaction equation

HRID 1973412 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[NH:10][CH:11]=[C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:4].C(Cl)(Cl)Cl.[Br:27]Br>N1C=CC=CC=1>[Br:27][C:8]1[S:7][C:6]([NH:10][CH:11]=[C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:9]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24408BromineHCID 2808585HCID 2808585, compound

Product 1

HCID 13217732HCID 13217732, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3.3 parts of diethyl (3-methoxycarbonylthienyl)aminomethylenemalonate in a mixture of 20 parts by volume of chloroform and 4 parts by volume of pyridine, 0.6 part by volume of bromine is added dropwise. The solution is further stirred at room temperature for 15 minutes, after which the reaction mixture is washed with dilute hydrochloric acid, an aqueous sodium hydrogen carbonate solution and water, followed by drying over Na2SO4. The solvent is distilled off to give diethyl (5-bromo-3-methoxycarbonylthienyl)aminomethylenemalonate. Recrystallization from ethanol gives light-yellowish needles melting at 129°-130° C.

Workup

  1. additionis added dropwise
  2. washafter which the reaction mixture is washed with dilute hydrochloric acid
  3. dry with materialby drying over Na2SO4
  4. distillationThe solvent is distilled off

Sources & evidence

ORD record
ord-c0c3173d2b4242cbb2e4d91bca7b7af3
Source dataset
uspto-grants-1976_12
Patent number
US03997545

Reaction notes

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