Bromine → HCID 67070992, compound

HRID 732076Notes

Reaction equation

HRID 732076 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([CH2:13][S:14][C:15]3[N:19]([CH3:20])[CH:18]=[N:17][N:16]=3)[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:21]Br>C(Cl)(Cl)Cl>[Br:21][C:18]1[N:19]([CH3:20])[C:15]([S:14][CH2:13][C:11]2[O:10][N:9]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[N:12]=2)=[N:16][N:17]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 8837815HCID 8837815, compound

Product 1

HCID 67070992HCID 67070992, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
70 °C

Procedure

3-(3-Chloro-phenyl)-5-(4-methyl-4H-[1,2,4]triazol-3-ylsulfanylmethyl)-[1,2,4]oxadiazole was mixed with 30 ml of chloroform/pyridine(25/1) at room temperature. Then bromine in chloroform (0.5 ml) was added dropwise and the reaction mixture was heated at 70° C. overnight. The reaction mixture was diluted with chloroform and washed with saturated NH4Cl twice and the organic layer was dried with sodium sulfate, concentrated, the residue was triturated with diethyl ether to give the title compound (1.5 g, 57.5 %, yellow solid). 1H-NMR(CDCl3) d(ppm): 8.05 (s, 1H), 7.94 (d, 1H), 7.47(d, 1H), 7.43 (t, 1H), 4.66 (s, 2H) and 3.59 (s, 3H).

Workup

  1. washwashed with saturated NH4Cl twice
  2. dry with materialthe organic layer was dried with sodium sulfate
  3. concentrationconcentrated
  4. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-48249a335d3141f588563ef60b62dd30
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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