Chloroform → HCID 13217732, compound

HRID 1679112Notes

Reaction equation

HRID 1679112 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-70fbc46e94d14d6f9bf97df6adb2670f
Source dataset
uspto-grants-1978_03
Patent number
US04079060

Reaction notes

Loading…