Bromine → HCID 54096162, compound

HRID 580829Notes

Reaction equation

HRID 580829 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[N:9]=[N:10][S:11][C:12]=2[C:13]2[C:14]([NH:19][CH2:20][CH3:21])=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])(=O)C.[Na+].[Br:27]Br>C(O)(=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([C:8]2[N:9]=[N:10][S:11][C:12]=2[C:13]2[C:14]([NH:19][CH2:20][CH3:21])=[N:15][CH:16]=[C:17]([Br:27])[CH:18]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 57099143HCID 57099143, compound

Product 1

HCID 54096162HCID 54096162, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(2-chloropyridin-3-yl)-5-(2-ethylaminopyridin-3-yl)-1, 2, 3-thiadiazole (0.324 g) in acetic acid (4 mL) containing sodium acetate (0.098 g) was added dropwise a solution of bromine (0.185 g) in acetic acid (1 mL). After 5 minutes, the mixture was diluted with ethyl acetate, washed with aqueous potassium carbonate, dried, filtered and evaporated. Chromatography of the residue over silica gel (ethyl acetate/hexane/chloroform 1/3/0.5) gave 4-(2-chloropyridin-3-yl)-5-(2-ethylamino-5-bromo-pyridin-3-yl)-1, 2, 3-thiadiazole (0.329 g).

Workup

  1. washwashed with aqueous potassium carbonate
  2. customdried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-9e31554bbf244cbe95f741a01dac1168
Source dataset
uspto-grants-1999_07
Patent number
US05919779

Reaction notes

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