Sodium Methoxide → 4-[(4-Chloro-3-hydroxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

HRID 901156Notes

Reaction equation

HRID 901156 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[N:10]2[CH:14]=[N:13][N:12]=[CH:11]2)=[CH:4][C:3]=1[O:23]C(=O)C1C=CC=CC=1.C[O-].[Na+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([N:10]2[CH:11]=[N:12][N:13]=[CH:14]2)[C:15]2[CH:16]=[CH:17][C:18]([C:21]#[N:22])=[CH:19][CH:20]=2)=[CH:4][C:3]=1[OH:23]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 167492234-[(3-benzoyloxy-4-chlorobenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

Product 1

HCID 167492244-[(4-Chloro-3-hydroxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of benzoic acid 2-chloro-5-{[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]methyl}-phenyl ester (CAB02139, 1.13 g, 2.63 mmol) and sodium methoxide (500 mg) in methanol (20 mL) and water (5 mL) was heated to reflux for 30 minutes. After cooling to room temperature most of the solvent was removed under reduced pressure and concentrated sodium bicarbonate solution (20 mL) and ethyl acetate (50 mL) were added. The organic layer was separated, dried over sodium sulphate and the solvent was removed under reduced pressure. The resulting white powder was refluxed in ethyl acetate (10 mL, product did not dissolve completely). After cooling to room temperature the product was filtered off and dried under high vacuum. Yield: 412 mg (48%) white powder. 1H-NMR (400 MHz, d6-DMSO) δ=4.97 (s, 2H), 6.71-6.75 (m, 3H), 6.84 (d, J=2.0 Hz, 1H), 7.25 (d, J=8.2 Hz, 1H), 7.75 (d, J=9.0 Hz, 2H), 8.76 (s, 2H), 10.21 (s, 1H, —OH). LRMS (FAB+): 326.1 (100, [M+H]+).

Workup

  1. temperatureto reflux for 30 minutes
  2. customwas removed under reduced pressure and concentrated sodium bicarbonate solution (20 mL) and ethyl acetate (50 mL)
  3. additionwere added
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. customthe solvent was removed under reduced pressure
  7. temperatureThe resulting white powder was refluxed in ethyl acetate (10 mL, product
  8. dissolutiondid not dissolve completely)
  9. temperatureAfter cooling to room temperature the product
  10. filtrationwas filtered off
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-bd45a269e7d949a8adbab46df899d8d0
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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