Triethylamine → 2-(4-bromo-5-chloro-2-methoxyphenyl)-2,4-dihydro-5-(5-bromothien-2-yl)-3H-1,2,4-triazol-3-one

HRID 2260926Notes

Reaction equation

HRID 2260926 reaction equation
[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][NH2:10])=[C:4]([O:11][CH3:12])[CH:3]=1.[Br:13][C:14]1[S:18][C:17]([C:19](=O)C(O)=O)=[CH:16][CH:15]=1.C([N:26]([CH2:29]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])C=CC=CC=1>C(#N)C>[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N:9]2[C:29](=[O:38])[NH:26][C:19]([C:17]3[S:18][C:14]([Br:13])=[CH:15][CH:16]=3)=[N:10]2)=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 144525865-Bromothiophene 2-Oxoacetic AcidHCID 22997648(4-Bromo-5-chloro-2-methoxyphenyl)hydrazine2×

Product 1

HCID 1358250532-(4-bromo-5-chloro-2-methoxyphenyl)-2,4-dihydro-5-(5-bromothien-2-yl)-3H-1,2,4-triazol-3-oneYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(4-Bromo-5-chloro-2-methoxyphenyl)hydrazine (Intermediate 2) (5.0 g) and 2-(5-bromothien-2-yl)glyoxylic acid (4.7 g) were refluxed in acetonitrile (15-25 ml/mmol starting material) for 30-60 minutes. The reaction was cooled to room temperature. Triethylamine (2.22 g) and diphenylphosphorylazide (6.05 g) were added, and the reaction was heated at reflux 3-18 hours. After cooling to room temperature, solids were filtered and washed with acetonitrile and ether to yield (75%) 2-(4-bromo-5-chloro-2-methoxyphenyl)-2,4-dihydro-5-(5-bromothien-2-yl)-3H-1,2,4-triazol-3-one (Intermediate 3).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux 3-18 hours
  3. temperatureAfter cooling to room temperature
  4. filtrationsolids were filtered
  5. washwashed with acetonitrile and ether

Sources & evidence

ORD record
ord-d25522b44d8649a587ac5c428f8dee3f
Source dataset
uspto-grants-2010_12
Patent number
US07846671B2

Reaction notes

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