Acetic Acid → HCID 178419415, compound

HRID 2401979Notes

Reaction equation

HRID 2401979 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([NH2:9])=O.COC(OC)[N:13]([CH3:15])C.C1(C)C=CC=CC=1.C(O)(=O)C.[NH2:29]N>>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[NH:9][CH:15]=[N:13][N:29]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 1140TolueneHCID 9321HydrazineHCID 78373Dimethylformamide dimethyl acetalHCID 6057213-Bromothiophene-2-carboxamide

Product 1

HCID 178419415HCID 178419415, compoundYield 85.6%

Conditions

Temperature
90 °C

Procedure

3-Bromothiophene-2-carboxamide (33.2 g, 161 mmol) in 1,1-dimethoxy-N,N-dimethylmethanamine (100 mL, 800 mmol) and toluene (100 mL, 900 mmol) was heated at 90° C. for 2 h. The solvent was evaporated off and the residue was dissolved in acetic acid (183 mL, 3220 mmol). Hydrazine (20 mL, 600 mmol) was added and the mixture was heated at 90° C. again. After 40 min, LCMS showed complete reaction. The reaction mixture was evaporated to remove most of the acetic acid. Water was added and the precipitate was collected and dried in air overnight to afford 3-(3-bromothiophen-2-yl)-4H-1,2,4-triazole as a white powder (31.7 g, 85.6%). LCMS: (FA) ES+ 230.0, 232.0

Workup

  1. customThe solvent was evaporated off
  2. customreaction
  3. customThe reaction mixture was evaporated
  4. customto remove most of the acetic acid
  5. additionWater was added
  6. customthe precipitate was collected
  7. customdried in air overnight

Sources & evidence

ORD record
ord-0d836c560e4c46f381812d183273f8eb
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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