Hydrochloric Acid → HCID 178516577, compound

HRID 1422867Notes

Reaction equation

HRID 1422867 reaction equation
COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][C:6]=1[C:21]1[N:22]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)[C:23]([SH:26])=[N:24][N:25]=1.Cl>CO>[SH:26][C:23]1[N:22]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)[C:21]([C:6]2[CH:7]=[C:8]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:9]([OH:11])=[CH:10][C:5]=2[OH:4])=[N:25][N:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178498574HCID 178498574, compound

Product 1

HCID 178516577HCID 178516577, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To the intermediate (400 mg, 0.77 mmol) was added degassed 2N—NaOH (0.7 mL, 0.35 mmol) and the reaction mixture was stirred at 110° C. for 2 h. After cooled down to room temperature, the reaction mixture was acidified with 1N—HCl. The white precipitate was filtered and dried to give 5-(4,6-Bis-methoxymethoxy-biphenyl-3-yl)-4-naphthalen-1-yl-4H-[1,2,4]triazole-3-thiol as a white solid (250 mg, 65%). 5-(4,6-Bis-methoxymethoxy-biphenyl-3-yl)-4-naphthalen-1-yl-4H-[1,2,4]triazole-3-thiol (190 mg, 0.38 mmol) was dissolved in MeOH (7 mL) and 6N—HCl (0.5 mL) was added to the solution. The reaction mixture was heated at 50° C. for 2 h. After MeOH was removed under vacuum, the reaction mixture was extracted with EtOAc (20 mL×3). The combined organic layers were washed with water and brine and dried over MgSO4. The purification of the concentrated crude product by column chromatography (MeOH 10% in CH2Cl2) afforded the title product as white solid (120 mg, 77%).

Workup

  1. customAfter MeOH was removed under vacuum
  2. extractionthe reaction mixture was extracted with EtOAc (20 mL×3)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe purification of the
  6. concentrationconcentrated crude product by column chromatography (MeOH 10% in CH2Cl2)

Sources & evidence

ORD record
ord-48a736d946d94add8628cf7306ab0404
Source dataset
uspto-grants-2015_01
Patent number
US08927548B2

Reaction notes

Loading…