Acetic Acid → 5-(5-Bromo-4-chloro-thiophen-2-yl)-1-methyl-[1,2,4]triazole

HRID 1432704Notes

Reaction equation

HRID 1432704 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:7]2[N:11]([CH3:12])[N:10]=[CH:9][N:8]=2)[S:5][CH:6]=1.C(#N)C.CC(O)=O.C1C(=O)N([Br:27])C(=O)C1>O>[Br:27][C:6]1[S:5][C:4]([C:7]2[N:11]([CH3:12])[N:10]=[CH:9][N:8]=2)=[CH:3][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 66721636HCID 66721636, compound

Product 1

HCID 667214755-(5-Bromo-4-chloro-thiophen-2-yl)-1-methyl-[1,2,4]triazoleYield 83.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 3-L reaction flask equipped with a cooling bath, air stirrer, and thermometer probe is charged with 5-(4-Chloro-thiophen-2-yl)-1-methyl-1H-[1,2,4]triazole (105.3 g, 0.527 moles), ACN (1053 mL) and HOAc (105 mL) to form a solution. NBS (103.2 g, 0.580 moles) is added portion-wise over 30-60 minutes while maintaining the temperature at ≦31° C. After stirring for 1 hour2, GC analysis indicated reaction completion. The reaction mixture is poured into de-ionized H2O (2.1 L, 20 vol), stirred for 30 minutes, filtered, and washed with de-ionized H2O (2×1 L). The product is dried in a vacuum oven at 45° C. overnight to give the title compound as a pale yellow solid (123.0 g, 83.8%; 96.6% area-% by GC). 2 The reaction temperature decreased after 1 hour to 26.7° C.

Workup

  1. customequipped with a cooling bath, air stirrer
  2. customto form a solution
  3. temperaturewhile maintaining the temperature at ≦31° C
  4. customreaction completion
  5. stirringstirred for 30 minutes
  6. filtrationfiltered
  7. washwashed with de-ionized H2O (2×1 L)
  8. customThe product is dried in a vacuum oven at 45° C. overnight

Sources & evidence

ORD record
ord-a8d4b8f983df4929a354362b07a663ad
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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