2-Bromo-5-phenyl-1,3,4-thiadiazole → HCID 22104434, compound

HRID 1457297Notes

Reaction equation

HRID 1457297 reaction equation
Br[C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][N:6]=1.[CH2:13]([Mg]Br)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C1COCC1.C1(P(C2C=CC=CC=2)C([Ni]Cl)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:13]([C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][N:6]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 131041172-Bromo-5-phenyl-1,3,4-thiadiazoleHCID 178443577HCID 178443577, compound

Product 1

HCID 22104434HCID 22104434, compound

Reagents, catalysts & solvents 2

HCID 178479584HCID 178479584, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Bromo-5-phenyl-1,3,4-thiadiazole (2.9 g, 12 mmol) is added to a 1-octylmagnesium bromide solution (4.6 g, 24 mmol) in THF (80 ml) under a protective-gas atmosphere, and 1,3-bis(diphenylphosphino)propylnickel(II) chloride (0.15 mmol), dissolved in . . . , is then added dropwise at -5° C. The mixture is subsequently stirred at this temperature for 4 hours. After acidification by means of hydrochloric acid (pH=2), the organic phase is separated off and evaporated. The crude product is recrystallized from acetonitrile.

Workup

  1. dissolutiondissolved in
  2. addition, is then added dropwise at -5° C
  3. customAfter acidification by means of hydrochloric acid (pH=2), the organic phase is separated off
  4. customevaporated
  5. customThe crude product is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-d4f7fabfe22c4a79b24ec12ab94bb75b
Source dataset
uspto-grants-1998_12
Patent number
US05847149

Reaction notes

Loading…