Hydrochloric Acid → HCID 21717674, compound

HRID 1386119Notes

Reaction equation

HRID 1386119 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[S:15][C:16](Br)=[C:17](Br)[C:18]=2[CH3:19])[N:11]([CH3:22])[N:10]=1.[ClH:23]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:13]=[C:12]([C:14]2[S:15][CH:16]=[C:17]([Cl:23])[C:18]=2[CH3:19])[N:11]([CH3:22])[N:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11317247HCID 11317247, compound

Product 1

HCID 21717674HCID 21717674, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Cuprous chloride (2.9 g) was added to a solution of 3-(2-chloro-6-fluorophenyl)-5-(3-methyl-4,5-dibromothien-2-yl) 1-methyl [1,2,4] triazole in DMF and heated at 120° C. for 12 h under a nitrogen atmosphere. After cooling, HCl (1N) was added and extracted with ether (3×100 mL), washed with brine, dried (Na2SO4), filtered and concentrated to give 1.35 g of crude solid. This was chromatographed on silica gel (Hexane/EtOAc, 3:1, 2:1, 1:1) gave 3-(2-chloro-6-fluorophenyl)-5-(3-methyl-4-chlorothien-2-yl) 1-methyl [1,2,4] triazole as white solid (0.6 g, 55%) MP 117-118° C.; Anal. Calcd. For C14H10BrClFN3S: C, 49.14; H, 2.95; N, 12.28; S, 9.37. Found; C, 48.86; H, 3.03; N, 12.04; S, 9.37.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ether (3×100 mL)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give 1.35 g of crude solid
  8. customThis was chromatographed on silica gel (Hexane/EtOAc, 3:1, 2:1, 1:1)

Sources & evidence

ORD record
ord-40e9c99fab1148cdb866646667302a58
Source dataset
uspto-grants-2001_07
Patent number
US06265424B1

Reaction notes

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