benzyl 3-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)phenylcarbamate → 3-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)aniline

HRID 2178593Notes

Reaction equation

HRID 2178593 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[N:21]([CH:22]3[CH2:24][CH2:23]3)[CH:20]=[N:19][N:18]=2)[CH:12]=1)C1C=CC=CC=1>Br>[CH:22]1([N:21]2[CH:20]=[N:19][N:18]=[C:17]2[C:13]2[CH:12]=[C:11]([NH2:10])[CH:16]=[CH:15][CH:14]=2)[CH2:24][CH2:23]1

Participants

3

Reactant 1

HCID 66851731benzyl 3-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)phenylcarbamate

Product 1

HCID 581030493-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)anilineYield 88.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

[3-(4-Cyclopropyl-4H-[1,2,4]triazol-3-yl)-phenyl]-carbamic acid benzyl ester (60 mg, 0.17 mmol) was dissolved in HBr solution (1 mL, 33% in acetic acid) and the reaction mixture was stirred overnight. The solvent was removed and the residue was neutralized with saturated sodium bicarbonate solution before being poured into brine. The aqueous phase was extracted 5 times with ethyl acetate. The organic phase was dried with sodium sulfate and the solvent was removed to obtain 3-(4-cyclopropyl-4H-[1,2,4]triazol-3-yl)-phenylamine as an off-white powder (30 mg, 88%). 201.1 (M+1). 1H NMR of HBr salt (DMSO) d 9.24 (s, 1H), 7.50-7.63 (m, 3H), 6.6-8.0 (br, 4H+H2O), 3.65 ppm (m, 1H), 1.05 (m, 4H).

Workup

  1. customThe solvent was removed
  2. additionbefore being poured into brine
  3. extractionThe aqueous phase was extracted 5 times with ethyl acetate
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-205d0826c1564a1fb5ecdb61d07c71cb
Source dataset
uspto-grants-2015_06
Patent number
US09067933B2

Reaction notes

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